CN115462385A - Herbicidal composition containing phenyl isoxazolines with optical activity and application - Google Patents

Herbicidal composition containing phenyl isoxazolines with optical activity and application Download PDF

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CN115462385A
CN115462385A CN202211122947.0A CN202211122947A CN115462385A CN 115462385 A CN115462385 A CN 115462385A CN 202211122947 A CN202211122947 A CN 202211122947A CN 115462385 A CN115462385 A CN 115462385A
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methyl
active ingredient
sodium
ethyl
herbicide
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杨吉春
关爱莹
崔东亮
刘长令
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Jiangsu Yangnong Chemical Co Ltd
Shenyang Sinochem Agrochemicals R&D Co Ltd
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Jiangsu Yangnong Chemical Co Ltd
Shenyang Sinochem Agrochemicals R&D Co Ltd
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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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides

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  • Agronomy & Crop Science (AREA)
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  • Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention relates to herbicidal compositions comprising at least one optically active phenylisoxazoline of formula (I) or an agriculturally acceptable salt or derivative thereof and at least one further compound selected from herbicidally active compounds and/or safeners, wherein the variables are defined according to the description.

Description

Herbicidal composition containing phenyl isoxazolines with optical activity and application
The application is a divisional application of the Chinese invention patent application, and the original application date is as follows: year 2019, month 10, day 23, application No.: 201911013281.3, inventive name: a herbicidal composition comprising an optically active phenyl isoxazoline and use thereof, publication No.: CN112690283A.
Technical Field
The invention belongs to the field of agricultural herbicides, and particularly relates to a weeding composition containing phenyl isoxazolines with optical activity and application thereof.
Background
For many highly effective herbicides, there is the problem that their compatibility with crops, especially dicotyledonous crops such as cotton, oilseed rape, and gramineous crops such as barley, millet, maize, rice, wheat and sugar cane is not always satisfactory, i.e. in addition to weeds, the crops are also damaged to some extent. By reducing the application rate, the crop is protected from damage; however, the extent of weed control is naturally also reduced. Has a broad herbicidal spectrum and is safe to crops, which can not be achieved by using a single herbicide.
The specific combination of herbicides of different mechanisms of action may be synergistic to enhance the activity of the herbicide component. In this way the application rate of the herbicide required for weed control can be reduced.
In addition, some high-efficacy herbicides can also be used in combination with safeners to achieve better crop compatibility and reduce or prevent damage to crops.
Some herbicidally active compounds having the general formula phenylisoxazoline structure have been disclosed in CN 105753853. There are no reports relating to the combination of optically active phenylisoxazolines with other herbicides or safeners.
Figure BDA0003847165890000011
Disclosure of Invention
The invention aims to provide a weeding composition containing phenyl isoxazolines with optical activity and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
the invention relates to a weeding composition which comprises an active component A and an active component B; or, active ingredient a and active ingredient C; or, active ingredient a, active ingredient B and active ingredient C;
the mass part ratio of the active component A to the active component B is 1; the mass part ratio of the active component A to the active component C is 1;
active ingredient a) at least one optically active phenylisoxazoline of formula (I):
Figure BDA0003847165890000012
in the formula:
* Carbon represents an asymmetric carbon atom, and the configuration of the asymmetric carbon atom can be R configuration (A1) or S configuration (A2);
R 1 is selected from CH 3 Or NH 2 ；
R 2 Selected from trifluoromethyl or difluoromethyl;
R 3 、R 4 are respectively selected from hydrogen, fluorine, chlorine or isopropoxy;
R 5 selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl;
R 6 is selected from CH 2 CO 2 R 7 、CH 2 CH 2 CO 2 R 7 Or CO 2 R 7 ；
R 7 Selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, trifluoromethyl, difluoroethyl, heptafluoroisopropyl, allyl, propargyl, 2-methylallyl, 1,1-dimethylallyl, cyclobutyl, propargyl, cyclopropyl, cyclohexyl, methoxyethyl, ethoxyethyl, isopropoxyethyl, CH 3 OCOCH 2 、CH 3 CH 2 OCOCH 2 、(CH 3 ) 2 CHOCOCH 2 、CH 3 OCOCH 2 CH 2 、CH 3 CH 2 OCOCH 2 CH 2 、(CH 3 ) 2 CHOCOCH 2 CH 2 、CH 3 OCOCH(CH 3 )、CH 3 CH 2 OCOCH(CH 3 ) Furan methylene or tetrahydrofuran methylene, benzyl unsubstituted or further substituted by 1-2 groups independently selected from: fluorine, chlorine, bromine, CN, NO 2 Methyl, isopropyl or tert-butyl;
an agriculturally acceptable salt or derivative including compounds of formula (I) having a carboxy group;
active ingredient B) at least one herbicide of the herbicide classes B (B1) -B15):
b1 Lipid biosynthesis inhibitors;
b2 Acetolactate synthase inhibitors (ALS inhibitors);
b3 A photosynthesis inhibitor;
b4 Protoporphyrinogen oxidase inhibitors (PPO inhibitors);
b5 Pigment synthesis inhibitors;
b6 5-enolpyruvylshikimate-3-phosphate synthase inhibitors (EPSP inhibitors);
b7 Glutamine synthetase inhibitors (GST inhibitors);
b8 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);
b9 ) mitotic inhibitors;
b10 Very long chain fatty acid synthesis inhibitors (VLCFA inhibitors);
b11 Cellulose biosynthesis inhibitors;
b12 Oxidative phosphorylation uncoupler herbicides;
b13 Hormone synthesis herbicides;
b14 Hormone transduction inhibitors; and
b15 Other herbicides) selected from the group consisting of: bromobutyric acid, chlordane (chloroflurenol), chlordane (chloroflurenol-methyl), cinmethylin (cinmethylin), cumyluron (cumyluron), dalapon (dalapon), dazomet (dazomet), difenzoquat (difenzoquat), difenzoquat sulfate (difenzoquat-metilsulfate), thionine (dimethipin) sodium arsonate (DSMA), vanillyl ketone (dymron), dichlobenil (endothal) and salts thereof, ethacryl (etobenzanid), trifluralin (flamprop), fluazinam (flamprispropopyl), fluazinam (flamprop-methyl), difloram (flamprop-M-isoproyl), lolium (flamprop-M-methyl), butanic acid (flurenol) flufenadine (flurenol-butyl), pyrimethanil (flurprimidol), fosfamine (fosamine), fosamine-ammonium (fosamine-ammonium), indanthrone (indofenan), indanfluzam (indazlactam), carbostyril (maleic hydrazide), flurazone (mefluidide), metam (metam), methyl azide (methyl azide), methyl bromide (methyl bromide), cumyluron (methyl-dymron), methyl iodide (methyl iodide), arsine monosodium (MSMA), oleic acid (oleic acid), chlorazine (oxazilomene), pelargonic acid (pelargonic acid), pyributicarb (pyributicarb), quinoxalone (quinofenadine), propylamine (triazifluorine), pyrimethanil (cyclocaryophylline), pyrimethamine (cyclocaryophylline), methiozolin and tetflupyrlomet;
including agriculturally acceptable salts or derivatives thereof.
The active ingredient C is a safener, which may be selected from the group consisting of (quinoline-8-oxy) acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acid, dichloroacetamides, α -hydroxyiminophenylacetonitrile, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N- [ [4- (aminocarbonyl) phenyl ] sulfonyl ] -2-benzamides, 1,8-naphthalic anhydride, 2-halo-4-haloalkyl-5-thiazolecarboxylic acid, thiophosphates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and agriculturally acceptable derivatives such as amides, esters and thioesters, provided they have an acid group. Including salts or derivatives thereof.
The phenylisoxazolines of the formula (I) have one chiral center, it being possible to use the R-and S-isomers A1 and A2 in the compositions according to the invention.
Preferred compounds of phenylisoxazolines of the formula (I) in which the variables have the following meanings, independently of one another or in combination with one another:
* Carbon represents an asymmetric carbon atom, and the configuration of the carbon atom can be R configuration (A1) or S configuration (A2);
R 1 is selected from CH 3 ；
R 2 Is selected from trifluoromethyl;
R 3 、R 4 are respectively selected from hydrogen, fluorine, chlorine or isopropoxy;
R 5 selected from hydrogen or methyl;
R 6 is selected from CH 2 CO 2 R 7 、CH 2 CH 2 CO 2 R 7 Or CO 2 R 7 ；
R 7 Selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, methoxyethyl, ethoxyethyl, furanmethylene or tetrahydrofurmethylene.
* The central carbon atom at the label is an asymmetric carbon atom or a chiral carbon atom, and four different substituents on the central carbon atom can be in the R configuration or the S configuration according to the nomenclature of the R-S system adopted by IUPAC.
Further preferred is a phenylisoxazoline compound of formula (I) in the R configuration (A1);
further preferred is a phenylisoxazoline compound of formula (I) in S configuration (A2);
particularly preferred compounds (I) according to the invention can be illustrated by, but are not limited to, the specific compounds listed in Table A. Compounds in the tables R 1 ＝CH 3 ，R 2 ＝CF 3 And other groups are shown in the table.
Figure BDA0003847165890000031
Active ingredient A Compounds of part A of Table A
Figure BDA0003847165890000032
Figure BDA0003847165890000041
Figure BDA0003847165890000051
Figure BDA0003847165890000061
Figure BDA0003847165890000071
Figure BDA0003847165890000081
The herbicide B may be selected from a lipid biosynthesis inhibitor (herbicide B1). Such compounds are compounds that inhibit lipid biosynthesis. Inhibition of lipid biosynthesis can be carried out by inhibition of acetyl-CoA carboxylase (hereinafter referred to as ACC herbicide) or by different modes of action (hereinafter referred to as non-ACC herbicide). ACC herbicides belong to class a of the HRAC classification system, whereas non-ACC herbicides belong to class N of the HRAC classification.
The herbicide B may be selected from an ALS inhibitor (herbicide B2). The herbicidal activity of such compounds is based on the inhibition of acetolactate synthase and thus on the inhibition of branched-chain amino acid biosynthesis. These inhibitors belong to class B of the HRAC classification system.
The herbicide B may be selected from a photosynthesis inhibitor (herbicide B3). The herbicidal activity of such compounds is based on the inhibition of the photosynthesis system II in plants (so-called PSII inhibitors, class C1, C2 and C3 of the HRAC classification) or on the diversion of electron transfer in the photosynthesis system I in plants (so-called PSI inhibitors, class D of the HRAC classification) and thus on the inhibition of photosynthesis. Among them, PSII inhibitors are preferred.
The herbicide B may be selected from a protoporphyrinogen oxidase inhibitor (herbicide B4). The herbicidal activity of such compounds is based on the inhibition of protoporphyrinogen oxidase. These inhibitors belong to class E of the HRAC classification.
The herbicide B may be selected from a pigment synthesis inhibitor herbicide (herbicide B5). The herbicidal activity of such compounds is based on the inhibition of carotenoid biosynthesis. These include compounds which inhibit carotenoid biosynthesis by inhibiting phytoene dehydrogenase (so-called PDS inhibitors, class F1 of the HRAC classification), compounds which inhibit 4-hydroxyphenylpyruvate dioxygenase (HPPD inhibitors, class F2 of the HRAC classification), compounds which inhibit DOX synthase (class F4 of the HRAC classification) and compounds which inhibit carotenoid biosynthesis by an unknown mode of action (pigment synthesis inhibitors-unknown targets, class F3 of the HRAC classification).
The herbicide B may be selected from an EPSP synthase inhibitor (herbicide B6). The herbicidal activity of such compounds is based on the inhibition of 5-enolpyruvylshikimate-3-phosphate synthase and thus on the inhibition of amino acid biosynthesis in plants. These inhibitors belong to class G of the HRAC classification system.
The herbicide B may be selected from a glutamine synthetase inhibitor (herbicide B7). The herbicidal activity of such compounds is based on the inhibition of glutamine synthetase and thus on the inhibition of amino acid biosynthesis in plants. These inhibitors belong to class H of the HRAC classification system.
The herbicide B may be selected from a DHP synthase inhibitor (herbicide B8). The herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase. These inhibitors belong to class I of the HRAC classification.
The herbicide B may be selected from a mitotic inhibitor (herbicide B9). The herbicidal activity of these compounds is based on the perturbation or inhibition of microtubule formation or organization and thus on the inhibition of mitosis. These inhibitors belong to the K1 and K2 classes of the HRAC classification. Among them, K1 compounds, particularly dinitroanilines, are preferable.
The herbicide B may be selected from a VLCFA inhibitor (herbicide B10). The herbicidal activity of such compounds is based on the inhibition of the synthesis of very long chain fatty acids and thus on the perturbation or inhibition of cell division in plants. These inhibitors belong to the K3 class of the HRAC classification.
The herbicide B may be selected from a cellulose biosynthesis inhibitor (herbicide B11). The herbicidal activity of such compounds is based on the inhibition of cellulose biosynthesis and thus on the inhibition of cell wall synthesis in plants. These inhibitors belong to the L class of the HRAC classification system.
The herbicide B may be selected from a phosphine oxide acidification uncoupler herbicide (herbicide B12). The herbicidal activity of such compounds is based on interference of cell membranes. These inhibitors belong to class M of the HRAC classification.
The herbicide B may be selected from a hormone-synthesizing class of herbicides (herbicide B13). This class includes compounds that mimic auxin, a plant hormone, and affect plant growth. These compounds belong to the O class of the HRAC classification system.
The herbicide B may be selected from a hormone transduction inhibitor (herbicide B14). The herbicidal activity of such compounds is based on the inhibition of auxin transport in plants. These compounds belong to class P of the HRAC classification system.
The herbicide B may be selected from other unknown mechanisms of action (herbicide B15). The compounds belong to the Z class of the HRAC classification system. For a given mechanism of action and classification of the active substances, see, for example, "HRAC, herbicide classification according to mode of action", http:// www.plantprotection.org/HRAC/moa. Html).
The herbicides b1 to b15 described above are specifically:
b1 A lipid biosynthesis inhibitor selected from the group consisting of: <xnotran> ACC (alloxydim), (alloxydim-sodium), (butroxydim), (clethodim), (clodinafop), (clodinafop-propargyl), (cycloxydim), (cyhalofop), (cyhalofop-butyl), (diclofop), (diclofop-methyl), (fenoxaprop), (fenoxaprop-ethyl), (fenoxaprop-P), (fenoxaprop-P-ethyl), (fluazifop), (fluazifop-butyl), (fluazifop-P), (fluazifop-P-butyl), (haloxyfop), (haloxyfop-methyl), (haloxyfop-P), (haloxyfop-P-methyl), (metamifop), (pinoxaden), (profoxydim), (propaquizafop), (quizalofop), (quizalofop-ethyl), (quizalofop-tefuryl), (quizalofop-P), (quizalofop-P-ethyl), (quizalofop-P-tefuryl), </xnotran> Sethoxydim (sethoxydim), tepraloxydim (tepraloxydim), tralkoxydim (tralkoxydim); and non-ACC herbicides such as benfuresate (benfuresate), butachlor (butylate), chloral (cyclate), dalapon (dalapon), dimepiperate (dimepipe), prometryn (EPTC), esprocarb (esprocarb), ethofumesate (ethofumesate), tetrafluoropropionic acid (fluproparate), molinate (molinate), turfgrass (orbetacarb), kekum (pebulate), prosulfocarb (prosulfocarb), TCA, thiobencarb (thiobencarb), ding Caowei (tiocarbzil), triallate (triallete) and vernolate (vernolate);
b2 ALS inhibitors selected from the group consisting of: <xnotran> , (amidosulfuron), (azimsulfuron), (bensulfuron), (bensulfuron-methyl), (chlorimuron), (chlorimuron-ethyl), (chlorsulfuron), (cinosulfuron), (cyclosulfamuron), (ethametsulfuron), (ethametsulfuron-methyl), (ethoxysulfuron), (flazasulfuron), (flucetosulfuron), (flupyrsulfuron), (flupyrsulfuron-methyl-sodium), (foramsulfuron), (halosulfuron), (halosulfuron-methyl), (imazosulfuron), (iodosulfuron), (iodosulfuron-methyl-sodium), iofensulfuron, iofensulfuron-sodium, (mesosulfuron), metazosulfuron, (metsulfuron), (metsulfuron-methyl), (nicosulfuron), (orthosulfamuron), (oxasulfuron), (primisulfuron), (primisulfuron-methyl), propyrisulfuron, (prosulfuron), (pyrazosulfuron), (pyrazosulfuron-ethyl), (rimsulfuron), (sulfometuron), (sulfometuron-methyl), (sulfosulfuron), </xnotran> Thifensulfuron-methyl (thifensulfuron), thifensulfuron-methyl (thifensulfuron-methyl), triasulfuron (triasulfuron), tribenuron-methyl (tribenuron-methyl), trifloxysulfuron (trifloxysulfuron), triflusulfuron (triflusulfuron-methyl), monosulfuron (monosulfuron-ester), and triflusulfuron (tritosulfuron), imidazolinones such as imazamethabenz (imazamethabenz), imazamethabenz (imazamethabenz-methyl), imazamox (imazamox), imazapyr (imazamethabenz-methyl), imazaquine (imazamox), and imazapyr (imazapyr), triazolopyrimidine herbicides and sulfonanilides such as diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisufan and pyroxsulam, pyrimidinylbenzoates such as dipyridamole benzoic acid (bispyribac), dipyridamole sodium benzoate (bispyribac-sodium), pyribenzoxim (pyribenzoxim), pyribenzoxim (pyriftalid), pyribenzoxim (pyriminobac-methyl), pyrithiobac (pyrithiobac), pyrithiobac-sodium (pyrithiobac-sodium), sulfonylaminocarbonyltriazolinones such as flucarbazone (flucarbazone), flucarbazone sodium (flucarbazone sodium), tribenuron-methyl (propxyarbazone), tribenuron-methyl sodium (propxyarbazone-sodium), thiencarbazone and thiencarbazone-methyl, and triafamone (triafamone);
b3 A photosynthesis inhibitor selected from: amicarbazone (amicarbazone), triazine herbicides including chlorotriazines, triazinones, triazindiones, methylthiotriazines and pyridazinones, such as ametryn, atrazine, chlorfenapyr, cyanazine, dimetrazine, dimethomon, hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbutryn, terbumetone, terbutryn and metribuzin; arylureas such as chlorobromoron (chlorobromon), saflufenacil (saflufenacil), cuminum (chloroxuron), ding Long (dimefuron), diuron (diuron), fluometuron (fluometuron), isoproturon (isoproturon), isoproturon (isouron), linuron (linuron), metamitron (metamitron), metabenzhiuron (methabenzthiazuron), chroman (metobenazuron), metoxuron (metoxuron), chlorsulfuron (monolinuron), mesoron (neburon), cyhaloron (siduron), tebuchiuron (tebuthiuron) and thidiazuron (thidiazuron), phenylcarbamates such as isoxadifenon (desmethyl), bencaedipham (diphenpyrane), phenmedipham (phendimethyn), phenmedipham (diphenpyra-mefenoxate), nitrile herbicides such as bromofenoxim (bromoxynil), bromoxynil (bromoxynil) and salts and esters thereof, ioxynil (ioxynil) and salts and esters thereof, cyclopyranil, uracils such as bromacil (bromoacil), lenacil (lenacil) and terbacil (terbacil), and bentazone (bentazone), bentazone sodium salt (bentazone-sodium), pyridate (pyridafone), pyridafone, phytolachlor (pentachlor) and propanil (propanil) and photosystem I inhibitors such as diquat (diquat), diquat-dibromide (diquat-dibromide), paraquat (paraquat), paraquat dichloride (paraquat-dichloride) and paraquat sulfate (paraquat-dimethomolide);
b4 Protoporphyrinogen oxidase inhibitors selected from the group consisting of: acifluorfen (acifluorfen), acifluorfen sodium salt (acifluorfen-sodium), carfentrazone (azafenidin), bencarbazone (benfendizone), bifenox (bifenox), butafenacil (butafenacil), carfentrazone acid (carfentrazone), carfentrazone-ethyl, chloronitrofen (chlorohexfen), and mixtures thereof Chlorpthhalim, cinidon-ethyl, pyriflufen-ethyl, flufenoxaprop-ethyl, flufenoxyfen-ethyl, imidophenoxyacetic acid (fluiclorac), imidophenoxyacetic acid pentyl ester (fluiclorac-pentyi), flufenoxazin (flunixazin) fluoroglycofen (fluoroglycofen), fluoroglycofen-ethyl (fluoroglycofen-ethyl), propaquizafop (fluthiacet), mefenacet-methyl (fluthiacet-methyl), fomesafen (fomesafen), nitrofen (halosafen), lactofen (lactofen), oxadiargyl (oxadiargyl), oxadiazon (oxadiargyl), oxyfluorfen (oxyfluorfen), penconazole (pentoxazone), flumetsulam (profluorazole), pyraclonil (pyraclonil), pyraflufen-ethyl (pyraflufen), flumetsulam (sulfadiazine), thiadiazoline (thiamethoxam), thiabendazole-ethyl (thiabendazole), and trifloxystrobin (trifloxystrobin-ethyl);
b5 A pigment synthesis inhibitor herbicide selected from the group consisting of: (ii) a PDS inhibitor: beflubutamid (beflubutamid), flubutamid-M (beflubutamid-M), diflufenican (diflufenican), flurtamone (fluridone), flurtamone (flurochlorodone), flurtamone (flurtamone), norflurazon (norflurazon), flupyrazamide (picolinafen), HPPD inhibitors: bicyclotrione (benzobicyclon), pyroxadim (benzofenap), fluoxydim (bicyclopyrone), clomazone (clomazone), fenquinzone, bixozone (CAS 3238 zft 3238-95-9), isoxaflutole (isoxaflutole), mesotrione (mesotrione), oxozone (CAS 3262 zft 3262-21-3), pyrasulfotole, pyrazolynate (pyrazolynate), pyrazoxazole (pyrazoxyfen), sulcotrione (sulcotrione), tefuryltrione, tembotrione, tolpyralate, lancotrione, topramezone, quione, mequintocetone, pyrafluquinate, quinclorac, cycloxydim, tembotrione, triazophone, and fenflurazole, among others: aclonifen (aclonifen), imazapyr (amitrole) and fluometuron (flumeturon);
b6 EPSP synthase inhibitors selected from the group consisting of: glyphosate (glyphosate), glyphosate isopropylamine salt (glyphosate-isopyrammonium), glyphosate potassium salt (glyphosate potassium salt), and glyphosate-trimethicium;
b7 A glutamine synthetase inhibitor selected from: bialaphos (bialaphos), bialaphos-sodium, glufosinate (glufosinate), glufosinate-ammonium (glufosinate-P), and glufosinate-ammonium;
b8 DHP synthase inhibitors selected from the group consisting of: asulam (asulam);
b9 A mitotic inhibitor selected from the group consisting of: compound of group K1: dinitroanilines such as flumioxazin (benzfluralin), dimethomorph (butralin), dinoamine (dinitramine), teflufen (ethalfluralin), fluazifop (fluhlorlalin), oryzalin (oryzalin), pendimethalin (pendimethalin), prodiamine (prodiamine) and trifluralin (trifluralin), phosphoramidates such as amifostine (amiphos), amifostine (amifostine-methyl) and glufosinate (butamiphos), benzoates such as dichlorotic acid (chlorethal), dichlorthol (chlorethasol-dimethy), pyridines such as dithiopyr (dithiopyr) and thiazopyr (thiazopyr), benzamides such as propathrin (pyrazamide) and butanamine (2), benzamides: imazapyr (carbetamide), chlorpropham (chlorpropham), fluazifop (flamprop), fluazifop (flamprispropyl), fluazifop-methyl (flamprop-methyl), norflurazon (flamprop-M-isopopyl), lolium (flamprop-M-methyl) and propham (propham);
b10 A VLCFA inhibitor selected from: chloroacetamides such as acetochlor (acetochlor), alachlor (alachlor), amidichlor, butachlor (butachlor), butachlor (dimethachloride), dimethenamid (dimethenamid-P), metazachlor (metazachlor), metolachlor (metolachlor), S-metolachlor (metolachlor-S), pethoxamid (pethoxamid), pretilachlor (pretilachlor), propachlor (propachlor), propisochlor (propiosochlor) and thielavine (theosylchlorine), hydroxyacetanilides (oxyacetanilides) such as flufenacet (flufenacet) and mefenacet (mefenacet), acetanilides such as metamifop (diphenamid), napropamide (naproxamide), naparamide (napropamide) and naproxamide (napropamide-M), tetrazolinones such as fentrazamide (fentrazamide) and other herbicides such as anilofos (anilofos), cafenstrole (cafenstrole), fenoxasulfone, ipfencarbazone, piprophos (piperophos) and roxen sulfone (pyroxasulfone);
b11 Cellulose biosynthesis inhibitor selected from the group consisting of: chloramber (chlorethaamid), dichlobenil (dichlobenil), fenchlorazole (flupoxam), indoxazole (indazflam), isoxachlor (isoxaben), fenxylamine (triaziflam);
b12 Phosphine oxide acidification uncoupler herbicides selected from the group consisting of: dinotefuran (dinoseb), dinotefuran (dinoterb), dinitrocresol (DNOC), and salts thereof;
b13 ) hormone-synthesizing herbicides selected from the group consisting of: 2,4-D and salts and esters thereof, such as chlorophosphine (clacyfos), 2,4-D B and salts and esters thereof, aminocyclopyrachlor and salts and esters thereof, ammonidine (amiloride) and its salts such as amiloride dimonium (amiloride-dimonium), amiloride isopropanolate (2-hydroxy-propyl) ammonium) and its esters, benazolin (benazolin), benazolin-ethyl (benazolin-ethyl), chloramben (chlorimben) and its salts and esters, clomeprop (clomeprop) clopyralid (clopyralid) and salts and esters thereof, dicamba (dicamba) and salts and esters thereof, 2,4-dichlorprop (dichlorprop) and salts and esters thereof, 2,4-dichlorprop (dichlorprop-P) and salts and esters thereof, fluoropyrauxifen, fluroxypyr butoxypropyl (fluroxypyr-butoxymethyl) fluroxypyr-meptyl, fluroxypyr ester (halauxifen) and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, 2 methyl 4 chloroethyl thioester (MCPA-thioethyl), MCPB and its salts and esters, 2 methyl 4 chloropropionic acid (mecoprop) and its salts and esters, high 2 methyl 4 chloropropionic acid (mecoprop-P) and its salts and esters, picloram (picloram) and its salts and esters, quinclorac, quinmerac acid (quinmerac), TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, flurpropyridyl acid (flouxifen) and flurpyr-pyridate (florxafen-benzyl) (CAS 32 zxft 3732-72-379);
b14 Hormone transduction inhibitors selected from the group consisting of: diflufenzopyr, diflufenzopyr-Long Na, naptalam, and naptalam-sodium;
b15 Other herbicides) selected from the group consisting of: bromobutyric acid (bromobutamide), chlordane (chloroflurenol-methyl), cinmethylin (cinmethylin), cumyluron (cumyluron), cyclopyromate (CAS 499223-49-3) and salts and esters thereof, dalapon (dalapon), dazomet (dazomet), dichlorphenate (difenzoquat) dichlorphenate (difenzoquat-metilsulfate), thionine (dimethipin), arsine sodium (DSMA), vanillyl ketone (dymron), dichlobenil (endothal) and salts thereof, ethacryl (etobenzanid), butandin (flurenol-butyl), pyrimethanil (flurprimol) phosphino-aminium (fosamine), phosphino-aminium (fosamine-ammonium), indoxacin (indoxacan), maleic hydrazide (malazide), fluroxypyr (mefluide), metam (metam), methyl azide (methyl azide), methyl bromide (methyl bromide), benzyl chloride (methyl-dymron), methyl iodide (methyl iodide), mearsonium Sodium (MSMA), oleic acid (oleic acid), chlorazine (oxaziclofone), pelargonic acid (pelargonic acid), pyributicarb (pyributicarb), quinome (quinoxaline) and mefenacet (trichophane), methiozolin (CAS 403640-27-7) and tetafloliomet.
Further preferred herbicides B in the composition are:
b1 A lipid biosynthesis inhibitor selected from the group consisting of: clethodim (clethodim), clodinafop-propargyl, cycloxydim (cycloxydim), cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden (pinoxaden), cycloxydim (profoxdim), propaquizafop-P-methyl quizalofop-P-ethyl, quizalofop-P-tefuryl (quizalofop-P-tefuryl), sethoxydim (sethoxydim), tepraloxydim (tepraloxydim), tralkoxydim (tralkoxydim), benfuresate (benfuresate), pipate (dimepipe), prometryn (EPTC), esprocarb (esprocarb), ethofumesate (ethofumesate), molinate (molinate), pencarb (orb), prosulfocarb (prosulfocarb), prosulfocarb (thiobencarb), and triallate (triallate);
b2 ALS inhibitors selected from the group consisting of: <xnotran> (amidosulfuron), (azimsulfuron), (bensulfuron-methyl), (bispyribac-sodium), (chlorimuron-ethyl), (chlorsulfuron), (cloransulammethyl), (cyclosulfamuron), (diclosulam), (ethametsulfuron-methyl), (ethoxysulfuron), (flazasulfuron), (florasulam), (flucarbazone-sodium), (flucetosulfuron), (flumetsulam), (flupyrsulfuron-methylsodium), (foramsulfuron), (halosulfuron-methyl), (imazamethabenz-methyl), (imazamox), (imazapic), (imazapyr), (imazaquin), (imazethapyr), (imazosulfuron), (iodosulfuron), (iodosulfuron-methyl-sodium), iofensulfuron, iofensulfuron-sodium, (mesosulfuron), metazosulfuron, (metosulam), (metsulfuron-methyl), (nicosulfuron), (orthosulfamuron), (oxasulfuron), (penoxsulam), (primisulfuron-methyl), (propoxycarbazon-sodium), </xnotran> <xnotran> propyrisulfuron, (prosulfuron), (pyrazosulfuron-ethyl), (pyribenzoxim), pyrimisulfan, (pyriftalid), (pyriminobac-methyl), (pyrithiobac-sodium), (pyroxsulam), (rimsulfuron), (sulfometuron-methyl), (sulfosulfuron), thiencarbazone-methyl, (thifensulfuron-methyl), (triasulfuron), (tribenuron-methyl), (trifloxysulfuron), (triflusulfuron-methyl), (monosulfuron), (monosulfuron-ester), (tritosulfuron) (triafamone); </xnotran>
b3 A photosynthesis inhibitor selected from: ametryn (ametryn), amicarbazone (amicarbazone), atrazine (atrazine), bentazone (bentazone), bentazone sodium salt (bentazone-sodium), bromoxynil (bromoxynil) and salts and esters thereof, chlorfenadine (chloridazone), saflufenacil (saflufenacil), cyanazine (cyanazine), isoxaben (desmedipham), diquat-dibromide (diuron), fluometuron (fluometuron), hexazinone (hexazinone), ioxynil (ioxynil) and salts and esters thereof cyclopyranil, isoproturon, lenacil, linuron, metamitron, thidiazuron, metribuzin, propyzazine, paraquat, phenothrix, propanil, pyridate, simazine, terbutryn, terbuthylazine, thidiazene, thidiazuron, metribuzin, terbutryn, thidiazuron, etc
b4 Protoporphyrinogen oxidase inhibitors selected from the group consisting of: acifluorfen (acifluorfen-sodium), benciazone, benflurazone (benfendizone), butafenacil (butafenacil), carfentrazone-ethyl, cinidon-ethyl, flupyridaphenthrin (flufenpyr-ethyl), imidafenacet (fluiclorac-pentyl), flumioxazin (flufenoxaprop-ethyl), fluoroglycofen (fluoroxyflumetofen), fluoroglycofen (fluoroglycofen-ethyl), flufenpyr (fomesafen), fluorofenoxaprop (oxadiargyl), oxadixyl (oxypyr), oxyfluorfen (oxyfluorfen), pentoxazone (penfenpyr), fluoroxafen (flufenpyr-ethyl), oxadixyl (oxadiargyl), oxadixyl (oxadixyl), fluoroxyfen (oxadixyl), fluoroxyfluroxypyr), penflufen (oxadixyl), flufenpyr (fenpyr-ethyl), flumetsulam (oxadixyl (flufenpyr-ethyl), flumetsulam (oxadixyl (flufen-ethyl);
b5 A pigment inhibitor herbicide selected from the group consisting of: <xnotran> (aclonifen), (amitrole), (beflubutamid), (beflubutamid-M), (benzobicyclon), (bicyclopyrone), (clomazone), (diflufenican), fenquinotrione, (flumeturon), (flurochloridone), (flurtamone), (isoxaflutole), (mesotrione), bixlozone, oxotrione (CAS 3242 zxft 3242-21-3), (norflurazon), (picolinafen), pyrasulfotole, (pyrazolynate), (sulcotrione), (topramezone), tefuryltrione, tembotrione, tolpyralate, lancotrione, , , , , , , ; </xnotran>
b6 EPSP synthase inhibitors selected from the group consisting of: glyphosate (glyphosate), glyphosate isopropylamine salt (glyphosate-isopyrammonium), and glyphosate potassium salt (glyphosate potassium salt);
b7 A glutamine synthetase inhibitor selected from: glufosinate (glufosinate), glufosinate-ammonium (glufosinate-P) and glufosinate-ammonium (glufosinate-ammonium);
b8 DHP synthase inhibitors selected from the group consisting of: asulam (asulam);
b9 ) a mitotic inhibitor selected from: flumetsulam (benfluralin), dithiopyr (dithiopyr), ethalfluralin (ethalfluralin), fluazinam (flamprop-isoproyl), norflurazon (flamprop-methyl), difloran (flamprop-M-isoproyl), lolium (flamprop-M-methyl), oryzalin (oryzalin), pendimethalin (pendimethalin), thiazopyr (thiazopyr) and trifluralin (trifluralin);
b10 A VLCFA inhibitor selected from: acetochlor (acetochlor), alachlor (alachlor), amidichlor, anilofos (anilofos), butachlor (butachlor), cafenstrole (cafenstrole), dimethenamid (dimethenamid-P), fentrazamide (fentrazamide), flufenacet (flufenacet), mefenacet (mefenacet), metazachlor (metazachlor), metolachlor (metolachlor), S-metolachlor (S-metolachlor), napropamide (napanilide), naparamide (naproxamide-M), pretilachlor (tipilelor), fenoxasulfolane (ipfenpyrane), rofenpyrazone (pyroxasulfone), and thiethylamine (theophyll)
b11 Cellulose biosynthesis inhibitor selected from the group consisting of: dichlobenil (dichlobenil), fentrazole (flupoxam), indoxazole (indaziflam), isoxaben (isoxaben), fenpropazine (triaziflam);
b12 Phosphine oxide acidification uncoupler herbicides selected from the group consisting of: dinotefuran (dinoseb), dinotefuran (dinoterb) and Dinitrocresol (DNOC) and salts thereof;
b13 ) hormone-synthesizing herbicides selected from the group consisting of: 2,4-D and its salts and esters, aminocyclopyrachlor (aminocyclopyrachlor) and its salts and esters, triamcinolone (aminopyralid) and its salts such as triamcinolone dimethyl ammonium salt (aminopyralid-dimethyl ammonium), triamcinolone isopropyl ammonium salt (2-hydroxypropyl ammonium) and its esters, clopyralid (clopyralid) and its salts and esters, dicamba (dicamba) and its salts and esters, 2,4-diproprionic acid (dichrpop-P) and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, homo2-methyl-4-chloropropionic acid (mecoprop-P) and its salts and esters, picloram and its salts and esters, quinclorac, triclopyr and its salts and esters, fluroxypyr-meptyl (CAS 1390661-72-9);
b14 Hormone transduction inhibitors selected from the group consisting of: difluoropyrazosulfuron (diflufenzopyr) and difluoropyrazopyrane Long Na (diflufenzopyr-sodium);
b15 Other herbicides) selected from the group consisting of: bromobutyric acid (bromobiude), cinmethylin (cinmethylin), cumyluron (cumyluron), cyclopyromate (CAS 499223-49-3) and salts and esters thereof, dalapon (dalapon), dichlorbenzuron (difenzoquat-methilfate), arsonium sodium (DSMA), cumuron (dymron) (= daimuron), indanthrone (indoofan), metam (metam), methyl bromide (methamide), metharsonol Sodium (MSMA), chlorazine (oxaziclome), pyributicarb (pyributicarb), metydine (tridione), methzozolidinin and tetupyrolin.
Further, in the composition, the preferred herbicides B are:
b1 A lipid biosynthesis inhibitor selected from the group consisting of: clodinafop-propargyl, cycloxydim (cycloxydim), cyhalofop-butyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, pinoxaden, clethodim (profoxydim), quizalofop-P-ethyl, sethoxydim (sethoxydim), tepraloxydim (tepraloxydim), tralkoxydim oxime (tralkoxydim), esprocarb (esprocarb), prosulfocarb (prosulfocarb), thiobencarb (thiobencarb) and triallate (triallate);
b2 ALS inhibitors selected from the group consisting of: bensulfuron-methyl, dipyridamole sodium benzoate (bispyribac-sodium), cyclosulfamuron (cyclosulfamuron), diclosulam (diclosulam), flumetsulam (flumetsulam), fluazimson (fluazimsulfuron-methyl-sodium), foramson (foramsulfuron), imazamox (imazamox), imazapic (imazapic), imazapyr (imazaquin), imazapyr (imazethapyr), pyridinuron (imazosulfuron), iodosulfuron (iodosulfuron), iodosulfuron-methyl sodium (iodosulfuron-methyl) iofensulfuron, iofensulfuron-sodium, mesosulfuron (mesosulfuron), metazosulfuron (methasulfuron), nicosulfuron (nicosulfuron), penoxsulam (penoxsulam), tribenuron (propofol-sodium), pyrisulfuron (pyrazosulfuron-ethyl), pyroxsulam (pyroxsulam), rimsulfuron (rimsulfuron), sulforon (sulfosulfuron), thiencarbazone (sulfosulfuron), thiencbazon-methyl, triflusulfuron (tritosulfuron), monosulfuron (monosulfuron), monosulfuron ester (monosulfuron-er), and triafamone (triafamone);
b3 A photosynthesis inhibitor selected from: ametryn (ametryn), atrazine (atrazine), diuron (diuron), fluometuron (fluometuron), hexazinone (hexazinone), isoproturon (isoproturon), linuron (linuron), metribuzin (metribuzin), paraquat cation (paraquat), paraquat tdichloride (propanil), terbutryn (terbutryn), terbuthylazine (terbutylazine), and cyclopyranil;
b4 Protoporphyrinogen oxidase inhibitors selected from the group consisting of: fluazinone (flumoxazin), oxyfluorfen (oxyfluorfen), pyrazoxol (pyraflufen), pyraflufen-ethyl (pyraflufen-ethyl), saflufenacil (saflufenacil), sulfentrazone (sulfentrazone), and triflumimoxazin;
b5 A pigment inhibitor herbicide selected from the group consisting of: bicyclotrione (benzobicyclon), imazapyr (amisole), bicyclopyrone (bicyclopyrone), clomazone (clomazone), diflufenican (diflufenican), fenquinoxone (biflurazone), bixozone, fluometuron (flumetoron), flurochloridone (flurochlororidone), isoxaflutole (isoxaflutole), mesotrione (mesotrione), oxozone (CAS 8978 zft 8978-21-3), flupyrazamide (picolinafen), sulcotrione (sulcotrione), tefuryltrione, tembotrione, topyralate, lanotrione, topramezone (toamepromone), quintocet, mequinate, quinflutolanilide, cycloxydim, tembotrione, triazophoron and fenflurazole;
b6 EPSP synthase inhibitors selected from the group consisting of: glyphosate (glyphosate), glyphosate isopropylamine salt (glyphosate-isopyrammonium), and glyphosate potassium salt (glyphosate potassium salt);
b7 A glutamine synthetase inhibitor selected from: glufosinate (glufosinate), glufosinate-ammonium (glufosinate-P) and glufosinate-ammonium (glufosinate-ammonium);
b9 ) a mitotic inhibitor selected from: pendimethalin (pendimethalin) and trifluralin (trifluralin);
b10 A VLCFA inhibitor selected from: acetochlor (acetochlor), anilofos (anilofos), cafenstrole (cafenstrole), dimethenamid-P (dimethenamid-P), fentrazamide (fentrazamide), flufenacet (flufenacet), mefenacet (mefenacet), metazachlor (metazachlor), metolachlor (metachlor), S-metolachlor (S-metolachlor), fenoxasulfone, ipfencycarbazone and roxysulfone (pyroxasulfone);
b11 Cellulose biosynthesis inhibitor selected from the group consisting of: indoxazine flufenamid (indaziflam), isoxachlor (isoxaben), and promethazine (triaziflam);
b13 ) hormone-synthesizing herbicides selected from the group consisting of: 2,4-D and its salts and esters, such as clophyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluorochloramine (fluroxypyr-meptyl), fluorochloropyridine ester (halauxifen-methyl), quinclorac (quinclorac), quinclorac (quinmerac), chlorofluoropyridine ester (florpyrauxifen-benzyl) (CAS 1390661-72-9);
b14 Hormone transduction inhibitors selected from the group consisting of: difluoropyrazosulfuron (diflufenzopyr) and difluoropyrazopyrane Long Na (diflufenzopyr-sodium);
b15 Other herbicides) selected from the group consisting of: cinmethylin (cinmethylin), cumuron (dymon) (= daimuron), indanthrone (indofenan), chlorazine (oxaziclomefone), methiozolin, and tetflupyrlomet.
Particularly preferred herbicides B are those defined above; in particular the herbicides listed in Table B below
TABLE B
Figure BDA0003847165890000161
Figure BDA0003847165890000171
Figure BDA0003847165890000181
The active ingredient C is at least one safener C.
Safeners are compounds which prevent or reduce damage to useful plants but do not have a significant effect on the herbicidal action of the herbicidally active components of the composition of the invention on unwanted plants. They can be applied before sowing (for example in the case of seed treatment, on shoots or seedlings) or else in the form of pre-emergence application or post-emergence application of the useful plants. The safener and the phenylisoxazolines of formula (I) and the herbicide B can be applied simultaneously or sequentially.
Suitable safeners can be selected from the group consisting of (quinoline-8-oxy) acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acid, dichloroacetamides, α -hydroxyiminophenylacetonitrile, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N- [ [4- (aminocarbonyl) phenyl ] sulfonyl ] -2-benzamides, 1,8-naphthalic anhydride, 2-halo-4-haloalkyl-5-thiazolecarboxylic acid, thiophosphates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such as amides, esters and thioesters, provided they have an acid group.
Preferably, the safener C may be selected from the group consisting of benoxacor (benoxacor), cloquintocet (cloquintocet), chlorfenapyr (cyclotrinil), cyprosulfamide (cyhalodiamide), dichlormid (dichlormid), dicyclonon, dietholate, fenchlorazole (fenchlorazole), fenclorim (fenclorim), fenclozole (fluxazole), fluxofenam (fluxofenim), furazolidone (isoxadifen), pyrroledioic acid (mefenpyr), mephenate, naphthalic anhydride (naphthalic anhydride), oxabetrinil (oxabetrinil), metacamid, 4-dichloroacetyl-1-oxa-4-azaspiro [4.5] decane (MON 4660, CAS 71526-07-3), 2,2,5-trimethyl-3-dichloroacetyl-1,3-oxazolidine (R-29148, CAS 52836-31-4) and N- (2-methoxybenzoyl) -4- [ (methylaminocarbonyl) amino ] benzenesulfonamide (CAS 129531-12-0).
More preferred safeners C may be selected from cloquintocet (benoxacor), cloquintocet (cloquintocet), cyprosulfamide (cypronamide), dichlormid (dichlormid), fenchlorazole (fenclozole), fenclorim (fenclorim), fenchlorazole (flurazole), fluxofenam (fluxofenam), flurazon (furilazole), isoxadifen (isoxadifen), pyrrodic acid (mefenpyr), naphthalic anhydride (naphthalic anhydride), oxabetrinil (oxabetrinil), mecamifen, 4-dichloroacetyl-1-oxa-4-azaspiro [4.5] decane (MON 4660, CAS 71526-07-3), 2,2,5-trimethyl-3-dichloroacetyl-1,3-oxazolidine (R-29148, CAS 5231-3425) and N-carbamoyl (3425) benzenesulfonamide (N-3425).
The most preferred safeners C may be selected from the group consisting of cloquintocet (benoxacor), cloquintocet (cloquintocet), cyprosulfamide (dichlormid), fenchlorazole (fenchlorazole), fenclorim (fenclorim), furazolidone (furilazole), isoxadifen (isoxadifen), pyrrodic acid (mefenpyr), naphthalic anhydride (naphthalic hydride), mecamifen, 4-dichloroacetyl-1-oxa-4-azaspiro [4.5] decane (MON 4660, CAS 71526-07-3), 2,2,5-trimethyl-3-dichloroacetyl-32 zxft-32-oxazolidine (R-29148, CAS 35836-31-4) and N- (2-methoxybenzoyl) -4-methylaminocarbonyl) amino ] benzenesulfonamide (CAS 3425-12-zft 340).
As component of the composition according to the invention, safeners C are preferably the compounds listed in Table C below.
Watch C
Figure BDA0003847165890000182
Figure BDA0003847165890000191
Where the active ingredients A, B, C are mentioned as having ionizable functional groups, they may also be used 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, do not have an adverse effect on the activity of the active compounds.
Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium ions, of alkaline earth metals, preferably calcium and magnesium ions, and of transition metals, preferably manganese, copper, zinc and iron ions, furthermore ammonium and the cations in which 1 to 4 hydrogen atoms have been replaced by C 1 -C 4 Alkyl, hydroxy-C 1 -C 4 Alkyl radical, C 1 -C 4 alkoxy-C 1 -C 4 Alkyl, hydroxy-C 1 -C 4 alkoxy-C 1 -C 4 Alkyl-, phenyl-or benzyl-substituted ammonium, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (alkanolamine salt), 2- (2-hydroxyethyl1-yloxy) ethan-1-ylammonium (diglycolamine salt), bis (2-hydroxyethyl1-ylammonium (diamine salt), tris (2-hydroxyethyl) ammonium (triol amine salt), tris (2-hydroxypropyl) ammonium, benzyltrimethylammonium, benzyltriethylammonium, N, N, N-trimethylethanolammonium(Choline salt), furthermore ions, sulfonium ions, preferably tris (C) 1 -C 4 Alkyl) sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tris (C) 1 -C 4 Alkyl) sulfoxonium, and finally salts of polyamines such as N, N-bis (3-aminopropyl) methylamine and diethylenetriamine.
The anions of the acid addition salts which are useful are predominantly chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also C 1 -C 4 The anion of an alkanoic acid, preferably formate, acetate, propionate and butyrate.
Alternatively, the A, B, C component described above may also be in the form of an acid, in the form of an agriculturally acceptable salt as described above, or in the form of an agriculturally acceptable derivative, e.g., as an amide, such as mono-and di-C 1 -C 6 Alkylamides or arylamides as esters, e.g. as allyl esters, propargyl esters, C 1 -C 10 Alkyl esters, alkoxyalkyl esters, tetrahydrofurylmethyl ((tetrahydrofuran-2-yl) methyl) esters and also as thioesters, e.g. as C 1 -C 10 Alkylthio esters are used. Preferred mono-and di-C 1 -C 6 Alkyl amides are methyl and dimethyl amides. Preferred aryl amides are, for example, anilide and 2-chloroanilide. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, methylhexyl (1-methylhexyl), methylheptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
Preferred is C 1 -C 4 alkoxy-C 1 -C 4 The alkyl ester being straight-chain or branched C 1 -C 4 Alkoxyethyl esters, for example 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butoxyethyl), 2-butoxypropyl or 3-butoxypropyl esters. Straight or branched C 1 -C 10 An example of an alkylthio ester is ethylthio ester.
b1 -B15) are known herbicides and safeners, see for example The Compendium of Pesticide Common Names (http:// www.alanwood.net/pesticides /); farm Chemicals Handbook 2000, volume 86, meister Publishing Company,2000; hock, c.fettke, r.r.schmidt, herbizide [ herbicides ], georg Thieme Verlag, stuttgart,1995; ahrens, herbicide Handbook, 7 th edition, weed Science Society of America,1994 and K.K. Hatzios, herbicide Handbook, 7 th edition supplement, weed Science Society of America,1998.2,2,5-trimethyl-3-dichloroacetyl-1,3-oxazolidine CAS number 52836-31-4 is also known as R-29148. 4-Dichloroacetyl-1-oxa-4-azaspiro [4.5] decane [ CAS number 71526-07-3] is also known as AD-67 and MON 4660.
The assignment of the corresponding mechanisms of action of the active compounds is based on prior knowledge. If several mechanisms of action are applicable to one active compound, the substance belongs to only one mechanism of action.
The active compounds B and C having carboxyl groups can be used in the compositions according to the invention in the form of the acids, agriculturally acceptable salts or agriculturally acceptable derivatives, as described above.
In the case of dicamba, suitable salts include those in which the counterion is an agriculturally acceptable cation. Suitable salts of dicamba are, for example, sodium dicamba (dicamba-sodium), potassium dicamba (dicamba-potassium), methyl ammonium dicamba (dicamba-methyl ammonium), dimethyl ammonium dicamba (dicamba-methyl ammonium), isopropyl ammonium dicamba (dicamba-isopropyl ammonium), diglycolamine dicamba (dicamba-diglylamine), ethanolamine dicamba (dicamba-olamine), diethanolamine dicamba (dicamba-diolamine), triethanolamine dicamba (dicamba-tromamine), dicamba-N, N-bis (3-aminopropyl) methylamine and dicamba-diethylenetriamine. Examples of suitable esters are dicamba methyl ester (dicamba-methyl) and dicamba butoxyethyl ester (dicamba-butyl).
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 dialolamine), 2,4-D triethanolammonium, 2,4-D isopropylammonium, 2,4-D triisopropanolammonium, 3584 zxft 84-D heptylammonium, 2,4-D dodecylammonium, 2,4-D tetradecylammonium, 2,4-D triethylammonium, 6262 zxft 62-D tris (2-hydroxypropyl) ammonium, 3556 zxft Triisopropylammonium, 3256 zxft 5756-D triethanolamine, 3838 zxft 345749, lithium zxft 5749. Examples of suitable esters of 2,4-D are 2,4-D butoxyethyl ester (2,4-D butoxyl), 2,4-D-2 butoxypropyl ester, 2,4-D-3-butoxypropyl ester, 2,4-D butyl ester (2,4-D-butyl), 2,4-D ethyl ester (2,4-D-e thy l), 2,4-D ethylhexyl ester (2,4-D-ethylhexyl ester), 2,4-D isobutyl ester (2,4-D isobutoxyl ester), 2,4-D isopropyloctyl ester (6258 zxft 58-D-isctyl ester), 58 zxft 6258-D-isopropyl ester (626258-6258-62xyz 6258), 2,4-D-propyl ester (6258-D-62xyz).
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 ester (2,4-DB-butyl) and 2,4-DB isooctyl ester (2,4-DB-isoctyl).
Suitable salts of 2,4-dichlorpropionic acid are, for example, 2,4-dichlorprop sodium (dichlorprop-sodium), 2,4-dichlorprop potassium (dichlorprop-potassium) and 2,4-dichlorprop dimethylammonium (dichlorprop-dichlorprop ammonium). Examples of suitable esters of 2,4-dipropionic acid are 2,4-butoxyethyl propionate (dichlorprop-butyl) and 2,4-isooctyl propionate (dichlorprop-isoctyl).
Suitable salts and esters of MCPA include MCPA butoxyethyl ester (MCPA-butyl), MCPA butyl ester (MCPA butyl), MCPA dimethylammonium, MCPA diethanolamine (MCPA-diolamine), MCPA ethyl ester (MCPA-ethyl), MCPA thioethyl ester (MCPA-thioethyl), MCPA-2-ethylhexyl ester (MCPA-2-ethylhexyl), MCPA isobutyl ester (MCPA-isobutryl), MCPA isooctyl ester (MCPA-isoctyl), MCPA isopropyl ester (MCPA-isocypyl), MCPA isopropyl ammonium, MCPA methyl ester (MCPA-methyl), MCPA ethanolamine (MCPA-olamine), MCPA potassium (MCPA-potassium), MCPA sodium (MCPA-sodium), and MCPA triethanolamine (MCPA triethanolamine).
A suitable salt of MCPB is sodium MCPB. A suitable ester of MCPB is MCPB ethyl ester (MCPB-ethyl).
Suitable salts of clopyralid are potassium clopyralid (clopyralid-potassium), ethanolammonium dichloropicolinate and triisopropanolammonium dichloropicolinate (2-hydroxypyropyl) ammonium). An example of a suitable ester of dichloropicolinic acid is dichloropicolinic acid methyl ester.
Examples of suitable esters of fluroxypyr are fluroxypyr and 2-butoxy-1-methylethyl fluroxypyr, with fluroxypyr being preferred.
Suitable salts of picloram are picloram dimethylammonium (picloram-dimethyllammonium), picloram potassium (picloram-potassium), picloram triisopropanolammonium (picloram-triisopropanolammonium) and picloram triethanolamine (picloram-tromamine). A suitable ester of picloram is picloram isooctyl ester (picloram-isoctyl).
A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are, for example, triclopyr-ethyl and triclopyr-butyl.
Suitable salts and esters of chloramben include chloramben-ammonium, diethanolamine, methyl-chloramben-methyl, methylammonium and sodium-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 triamcinolone include triamcinolone potassium (ammoniacal-potassium), triamcinolone dimethylammonium (ammoniacal-dimethylammonium), and triamcinolone isopropanolammonium (2-hydroxypropyl) ammonium).
Suitable salts of glyphosate are, for example, ammonium glyphosate, diammonium glyphosate, dimethylammonium glyphosate, isopropylamine glyphosate, potassium glyphosate, sodium glyphosate, sulfosate, and ethanolamine and diethanolamine salts, preferably diammonium glyphosate, isopropylamine glyphosate and potassium glyphosate.
A suitable salt of glufosinate is, for example, glufosinate-ammonium.
A suitable salt of glufosinate-P is for example glufosinate-ammonium (glufosinate-P-ammonium).
Suitable salts and esters of bromoxynil are, for example, bromoxynil butyrate (bromoxynil-butyrate), bromoxynil heptanoate (bromoxynil-heptanoate), bromoxynil octanoate (bromoxynil-octanoate), bromoxynil potassium (bromoxynil-potassium) and bromoxynil sodium (bromoxynil-sodium).
Suitable salts and esters of ioxynil are, for example, ioxonil octanoate, potassium ioxonil-potassium and sodium ioxonil.
Suitable salts and esters of 2 methyl 4 chloropropionic acid include butoxyethyl 2 methyl 4 chloropropionate (mecoprop-butoxyl), dimethylammonium 2 methyl 4 chloropropionate (mecoprop-dimethyllammonium), diethanolamine 2 methyl 4 chloropropionate (mecoprop-diolamine), mecoprop-ethadyl, 2 methyl 4 chloropropionic acid 2-ethylhexyl (mecoprop-2-ethylhexyl), isooctyl 2 methyl 4 chloropropionate (mecoprop-isoctyl), methyl 2 methyl 4 chloropropionate (mecoprop-methyl), potassium 2 methyl 4 chloropropionate (mecoprop-potassium), sodium 2 methyl 4 chloropropionate (mecoprop-sodium), and triethanolamine 2 methyl 4 chloropropionate (mecoprop-trolamine).
Suitable salts of homo-2-methyl-4-chloropropionic acid are, for example, homo-2-methyl-4-chloropropionate butoxyl (mecoprop-P-butoxyl), homo-2-methyl-4-chloropropionic acid dimethylammonium (mecoprop-P-dimethylammonioium), homo-2-ethylhexyl-2-methyl-4-chloropropionate (mecoprop-P-ethylhexyl), homo-2-methyl-4-chloropropionic acid isobutyl (mecoprop-P-isobutyl), homo-2-methyl-4-chloropropionic acid potassium and homo-2-methyl-4-chloropropionic acid sodium.
A suitable salt of difluoropyridone is, for example, difluoropyridone Long Na.
A suitable salt of triclopyr is, for example, sodium triclopyr (sodium).
Suitable salts and esters of aminocyclopyrachlor are, for example, dimethylammonium aminocyclopyrachlor, methyl aminocyclopyrachlor, triisopropanolammonium aminocyclopyrachlor, sodium aminocyclopyrachlor and potassium aminocyclopyrachlor.
A suitable salt of quinclorac is for example dimethyl ammonium quinclorac.
A suitable salt of quinmerac is for example dimethylammonium quinmerac.
A suitable salt of imazamox is for example ammonium imazamox.
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.
Suitable salts of imazethapyr are, for example, imazethapyr ammonium and imazethapyr isopropylammonium.
A suitable salt of topramezone is, for example, topramezone sodium.
The composition of the invention can be an active ingredient A and at least one active ingredient B; or at least one active ingredient a, at least one active ingredient B and at least one safener C;
wherein, when the active component B is selected from two or more than two, the herbicide is selected from herbicides with different action mechanisms.
The following are details of the compositions of the present invention in Table 1 below:
the compositions containing compound A1-3 are shown in Table 1, with compositions numbered 1-1 to 1-3760.
TABLE 1
Figure BDA0003847165890000221
Figure BDA0003847165890000231
Figure BDA0003847165890000241
Figure BDA0003847165890000251
Figure BDA0003847165890000261
Figure BDA0003847165890000271
Figure BDA0003847165890000281
Figure BDA0003847165890000291
Figure BDA0003847165890000301
Figure BDA0003847165890000311
Figure BDA0003847165890000321
Figure BDA0003847165890000331
Figure BDA0003847165890000341
Figure BDA0003847165890000351
Figure BDA0003847165890000361
Figure BDA0003847165890000371
Figure BDA0003847165890000381
Figure BDA0003847165890000391
Figure BDA0003847165890000401
Figure BDA0003847165890000411
Figure BDA0003847165890000421
Figure BDA0003847165890000431
Figure BDA0003847165890000441
Figure BDA0003847165890000451
Figure BDA0003847165890000461
Figure BDA0003847165890000471
Figure BDA0003847165890000481
Figure BDA0003847165890000491
Figure BDA0003847165890000501
Figure BDA0003847165890000511
Table 2: compositions comprising compound A2-3, wherein herbicide B and safener C are in accordance with B, C set forth in table 1, corresponding compositions numbered 2-1 to 2-3760.
Table 3: compositions comprising compound A1-5, wherein herbicide B and safener C are in accordance with B, C set forth in table 1, corresponding compositions numbered 3-1 to 3-3760.
Table 4: compositions comprising compound A2-5, wherein herbicide B and safener C are in accordance with B, C as listed in table 1, corresponding compositions numbered 4-1 to 4-3760.
Table 5: compositions comprising compounds A1-7, wherein herbicide B and safener C are in accordance with B, C set forth in table 1, corresponding compositions numbered 5-1 to 5-3760.
Table 6: compositions comprising compound A2-7, wherein herbicide B and safener C are in accordance with B, C set forth in table 1, corresponding compositions numbered 6-1 to 6-3760.
Table 7: compositions comprising compounds A1-12, wherein herbicide B and safener C are in accordance with B, C set forth in table 1, corresponding compositions numbered 7-1 to 7-3760.
Table 8: compositions comprising compound A2-12, wherein herbicide B and safener C are in accordance with B, C set forth in table 1, corresponding compositions numbered 8-1 to 8-3760.
The optically active compound of the general formula I related to the invention can be prepared from an optically active amino compound II by a method reported in the known literature, such as CN105753853, CN108570041 or WO2016095768 and the like.
Figure BDA0003847165890000512
The optically active amino compound II can be obtained by resolving a racemic amino compound III using a chiral column. Racemic amino compound III was prepared according to the method in CN 105753853.
Figure BDA0003847165890000513
Unless otherwise indicated, each group in the reaction formula is as defined above.
The invention also provides a weeding composition which can be used as a herbicide and is characterized in that the weeding composition is used as an effective component, and the weight content of the effective component is 1-99%. The herbicide preparation can be an aqueous emulsion, a dispersible oil suspending agent, a dispersible oil agent, a microemulsion, missible oil, a soluble agent, an aqueous solution, a suspending agent, a suspending emulsion, an ultra-low volume agent, powder, wettable powder, granules, water dispersible granules, dry suspending agent, microcapsule granules, effervescent tablets and water dispersible tablets. The composition of the invention can also be added with surface active substances such as an emulsifier, a dispersant, a wetting agent and the like, so as to increase the stability, permeability and wettability of the composition.
The dispersant suitable for preparing the composition of the present invention may be one or more of naphthalene or alkyl naphthalene formaldehyde condensate sulfonate, fatty alcohol ethylene oxide adduct sulfonate, alkylphenol polyoxyethylene ether sulfonate, polycarboxylate, fatty alcohol ethylene oxide adduct phosphate, alkylphenol polyoxyethylene, ether formaldehyde condensate sulfate, polyoxyethylene polyoxypropylene ether block copolymer, alkylphenol polyoxyethylene phosphate, lignosulfonate, gelatin, gum arabic, carboxymethyl cellulose, polyoxyethylene alcohol, polyvinylpyrrolidone, sodium polyacrylate, and polyethylene glycol.
The wetting agent suitable for preparing the composition of the present invention may be one or more of fatty alcohol sulfate, alkyl alcohol polyoxyethylene ether sodium sulfate, alkylphenol polyoxyethylene, ether sodium sulfate, alkylphenol polyoxyethylene ether formaldehyde condensate sulfate, alkyl sodium sulfate, alkyl naphthalene sulfonate, fatty alcohol ethylene oxide adduct sulfonate, alkylphenol formaldehyde condensate ethylene oxide adduct sulfonate, alkylamido sulfonate, fatty alcohol polyoxyethylene ether, alkylphenol polyoxyethylene ether, sorbitan fatty acid ester polyoxyethylene ether, polyoxyethylene polyoxypropylene ether block copolymer, and alkylphenol formaldehyde condensate polyoxyethylene ether.
Suitable solid carriers for preparing the compositions of the present invention may be clays, kaolin, gypsum, bentonite, diatomaceous earth, talc, china clay, magnesium aluminum silicate, activated clay, white carbon black, limestone, light calcium carbonate, corn starch, soluble starches, hexamethylenediammonium, benzofuran resins, styrene polymers and copolymers, and the like.
Suitable binders for preparing the herbicidal compositions of the present invention may be natural or synthetic, for example xanthan gum, gelatin, gum arabic, polyvinylpyrrolidone, magnesium aluminum silicate, polyvinyl alcohol, phenolic resins, shellac, carboxymethyl cellulose, methyl cellulose and sodium alginate. The defoaming agent can be natural killer, silicone, C 8～10 Fatty alcohol, C 10～20 Saturated fatty acids, amides, and the like.
The disintegrating agent suitable for preparing the composition of the invention can be one or more of calcium chloride, sodium sulfate, ammonium sulfate, polyethyl acrylate, sodium carbonate, polyvinylpyrrolidone, sodium alginate and sodium carboxymethyl starch.
Examples of preparation of the composition are:
i) Water soluble concentrates (SL, LS) 10 to 60 wt% of the composition of the invention and 5 to 15 wt% of a wetting agent (e.g. an alcohol alkoxylate) are dissolved in water and/or a water soluble solvent (e.g. an alcohol) added to 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersion Concentrate (DC) 5 to 25% by weight of the composition according to the invention and 1 to 10% by weight of a dispersant (e.g.polyvinylpyrrolidone) are dissolved in an organic solvent (e.g.cyclohexanone) added to 100% by weight. Dilution with water gives a dispersion.
iii) Emulsifiable Concentrates (EC) 15 to 70% by weight of the composition of the invention and 5 to 10% by weight of an emulsifier (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g. an aromatic hydrocarbon) added to 100% by weight. Diluting with water to obtain emulsion.
iv) emulsion (EW, EO, ES) 5 to 40% by weight of the composition of the invention and 1 to 10% by weight of an emulsifier (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 to 40% by weight of a water-insoluble organic solvent (e.g. an aromatic hydrocarbon). The mixture was introduced into water added to 100% by weight with the aid of an emulsifying machine and made into a homogeneous emulsion. Diluting with water to obtain emulsion.
v) suspension (SC, OD, FS) in a stirred ball mill 20 to 60% by weight of the composition according to the invention are comminuted with the addition of 2 to 10% by weight of dispersants and wetting agents (for example sodium lignosulphonates and alcohol ethoxylates), 0.1 to 2% by weight of thickeners (for example xanthan gum) and water to 100% by weight to give a finely divided active substance suspension. Dilution with water gives a stable suspension of the active substance. Up to 40 wt% binder (e.g. polyvinyl alcohol) is added for FS type compositions.
vi) Water-dispersible granules and Water-soluble granules (WG, SG) are finely ground to 50-80% by weight with the addition of dispersants and wetting agents (e.g. sodium lignosulfonates and alcohol ethoxylates) added to 100% by weight and made into water-dispersible or water-soluble granules by means of industrial units (e.g. extruders, spray towers, fluidized beds). 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% by weight of the composition according to the invention are ground in a rotor-stator mill with the addition of 1-5% by weight of a dispersant (e.g. sodium lignosulfonate), 1-3% by weight of a wetting agent (e.g. alcohol ethoxylate) and, to 100% by weight of a solid carrier (e.g. silica gel). Dilution with water gives a stable dispersion or solution of the active substance.
viii) gel (GW, GF) A fine suspension of the active substance is obtained by comminuting 5 to 25% by weight of the composition according to the invention in a stirred ball mill with addition of 3 to 10% by weight of a dispersant (for example sodium lignosulfonate), 1 to 5% by weight of a thickener (for example carboxymethylcellulose) and water to 100% by weight. Dilution with water gives a stable suspension of the active substance.
iv) Microemulsion (ME) 5-20 wt% of the composition of the invention is added to 5-30 wt% of an organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% of a surfactant blend (e.g. alcohol ethoxylate and aryl phenol ethoxylate) and to 100 wt% of water. The mixture was stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.
iv) microcapsules (CS) the oily phase comprising 5 to 50% by weight of the composition of the invention, 0 to 40% by weight of a water-insoluble organic solvent (for example an aromatic hydrocarbon), 2 to 15% by weight of acrylic monomers (for example methyl methacrylate, methacrylic acid and di-or triacrylates) is dispersed in an aqueous solution of a protective colloid (for example polyvinyl alcohol). The free radical polymerization initiated by the free radical initiator results in the formation of poly (meth) acrylate microcapsules. Or dispersing an oil phase comprising 5 to 50% by weight of the compounds I according to the invention, 0 to 40% by weight of a water-insoluble organic solvent (for example an aromatic hydrocarbon) and isocyanate monomers (for example diphenylmethane-4,4' -diisocyanate) in an aqueous solution of a protective colloid (for example polyvinyl alcohol). The addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomer is 1-10% by weight. The weight% relates to the entire CS composition.
ix) dustable powders (DP, DS) 1 to 10% by weight of the composition according to the invention are finely ground and intimately mixed with a solid carrier (for example finely divided kaolin) added to 100% by weight.
x) particles (GR, FG) 0.5 to 30% by weight of the composition of the invention is finely ground and combined with a solid carrier (e.g. silicate) added to 100% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed.
xi) ultra low volume liquids (UL) 1-50 wt% of the composition of the invention is dissolved in an organic solvent (e.g. an aromatic hydrocarbon) added to 100 wt%.
The above formulations i) -xi) may optionally comprise further auxiliaries, such as 0.1 to 1% by weight of a fungicide, 5 to 15% by weight of an antifreeze agent, 0.1 to 1% by weight of an antifoam agent and 0.1 to 1% by weight of a colorant.
The composition can be used as a herbicide in a using method, namely, the component A and the component B are separately, sequentially or simultaneously applied or the safener C is added, so that stem and leaf spraying treatment can be selectively or non-selectively carried out on weeds, burning waste before crop planting or after seeding emergence, and post-emergence treatment of tolerant crops and non-tolerant crops, and good control effect can be achieved.
The herbicidal compositions of the present invention are applied to the locus where undesirable vegetation is present or expected to be present, and may be applied selectively or non-selectively to the locus where undesirable vegetation is present or expected to be present. In particular, the fertilizer can be applied to soil in which the undesirable vegetation lives, stems and leaves of the undesirable vegetation, or burnout before the emergence of seedlings before planting or after sowing of crops, and post-emergence treatment of tolerant crops and non-tolerant crops.
The herbicide composition is applied to farmlands, uncultivated areas, orchards, rubber gardens, idle farmlands, rubber gardens, eucalyptus forests, fir forests, fire-proof roads, lawns, railways, highways, airports and warehouse places. The tolerant and non-tolerant crops are selected from rice, corn, legume crops, oilseed rape, vegetables, cotton, sugar beet, small grain cereals (including wheat, barley, oats, etc.), soybeans, peanuts, sugar cane, sunflowers, potatoes, cultivated crops, woody plants. The orchard comprises an apple orchard, a peach orchard, a grape orchard, a pear orchard, a tea orchard, a mulberry orchard and a citrus orchard. The undesirable vegetation includes grasses, broadleaf weeds, sedges, algae, ferns, and woody shrubs.
The composition provided by the invention has the following advantages:
1. the two active ingredients have very obvious synergistic effect, and the dosage of each component is reduced;
2. the composition has the characteristics of contact killing and systemic absorption by utilizing the complementation of different action mechanisms, increases the adaptability to adverse environments such as field drought, low temperature and the like, accelerates the reaction speed and realizes more thorough weeding;
3. the composition of the invention expands the application period, and particularly has enhanced continuous inhibition and prevention and control effects on broad-leaved weeds with larger leaf ages;
4. the composition has high control effect on glyphosate resistant weeds such as erigeron breviscapus, cynodon dactylon, eleusine indica and the like;
5. the spray treatment of the stem leaves of the composition can be used for preventing and removing most weeds in fields such as farmlands, uncultivated lands, orchards, idle farmlands, rubber gardens, eucalyptus forests, fire-proof roads, lawns, railways, highways, airports, warehouses and the like. Can also be used for preventing and killing weeds of corn, wheat, soybean, rice, cotton, potato and the like before or after seedling emergence.
6. The safener is added into the composition, so that the tolerance of crops is effectively increased, the phytotoxicity to the crops is reduced, and the convenience of using pesticides on the crops, such as corn, wheat, soybean, rice and the like, is improved.
Detailed Description
The synergistic effect of the compositions of the present invention on grasses and broadleaf weeds is further illustrated, but the invention is by no means limited, by the following examples, in which the active ingredients are compound a and glyphosate or agrochemically suitable salts and esters thereof in the herbicidal compositions of the present invention. The percentage of all preparation ratios is weight percentage, and the active ingredients are calculated by effective content. (all materials are commercially available unless otherwise noted)
Preparation example of active ingredient a:
EXAMPLE 1 preparation of Compounds A1-3 and A2-3
Figure BDA0003847165890000541
1) Preparation of ethyl (R/S) -3- (5-amino-2-chloro-4-fluorophenyl) -5-methyl-4,5-dihydro-5-isoxazolecarboxylate
25g of Amylose tris (3,5-dimethylphenylcarbamate) silica gel was loaded on a column, and 1g of a 5ml dichloromethane solution containing 1g of ethyl 3- (5-amino-2-chloro-4-fluorophenyl) -5-methyl-4,5-dihydro-5-isoxazolecarboxylate (prepared by the method described in CN 105753853) was adsorbed on the column, and the corresponding fractions were collected by Biotage flash preparative chromatography to give 0.47g (optical purity 99.8%, melting point 105-106 ℃) of ethyl optically isomeric (R) -3- (5-amino-2-chloro-4-fluorophenyl) -5-methyl-4,5-dihydro-5-isoxazolecarboxylate and 0.46g (optical purity 99.4%, melting point 104-104 ℃) of ethyl (S) -3- (5-amino-2-chloro-4-fluorophenyl) -5-methyl-4,5-dihydro-5-isoxazolecarboxylate.
Optical rotation [ alpha ]] 26℃ 589.44nm (Shen Guang WZZ-2S/2SS, sodium lamp wavelength: 589.44nm, solvent: acetonitrile): r isomer 150.65 °; s isomer-111.66 °.
2) Preparation of Compounds A1-3 and A2-3
0.45g (1.5 mmol) of ethyl (R) -3- (5-amino-2-chloro-4-fluorophenyl) -5-methyl-4,5-dihydro-5-isoxazolecarboxylate or (S) -3- (5-amino-2-chloro-4-fluorophenyl) -5-methyl-4,5-dihydro-5-isoxazolecarboxylate and 0.46g (1.8 mmol) of ethyl (Z) -3- (3,3-dimethylurea) -4,4,4-trifluorobutene-2-acetate (prepared by the method in CN 108570041) are added successively to a reaction flask containing 20ml of acetic acid, the reaction is warmed to reflux, kept at this temperature for 6h, desolvation under reduced pressure, the pH is adjusted to 7 by adding an aqueous sodium bicarbonate solution, ethyl acetate is extracted, the organic phase is dried over anhydrous magnesium sulfate and desolvated under reduced pressure, then 0.45g (3.24 mmol) of potassium carbonate and 5024 mmol of N-dimethylformamide are added successively to the residue, the mixture is stirred to room temperature of 0.51g of iodine, and then stirred to room temperature of methanol. After completion of the TLC monitoring reaction, the reaction mixture was poured into water, extracted with ethyl acetate, washed with saturated brine of the organic phase, dried over anhydrous magnesium sulfate, desolventized under reduced pressure, and subjected to column chromatography (ethyl acetate: petroleum ether = 1:5) to give compounds A1-3 and A2-3:0.48g, oil.
Optical rotation [ alpha ]] 20℃ 589.44nm (Shen Guang WZZ-2S/2SS, sodium lamp wavelength: 589.44nm, solvent: acetonitrile): a is 1-3 and 0.275 degrees; a2-3-0.243 degree.
Formulation examples
The active ingredients in the formula are metered in after being folded in hundred percent, and all the percentage contents are weight percentage contents.
Example 2 35% emulsifiable concentrate
Figure BDA0003847165890000551
Dissolving phosphorous acid in cyclohexanone, adding composition 1-40 and ethoxylated triglyceride, and obtaining transparent solution.
EXAMPLE 3 60% wettable powder
Figure BDA0003847165890000552
Mix composition 1-114, sodium dodecylnaphthalene sulfonate, sodium lignosulfonate and kaolin (all solids) together and grind in a grinder until the particles meet the standard.
Example 4 30% aqueous suspension
Figure BDA0003847165890000553
Compositions 1-114 were ground together with 80% of the amount of water to be added and sodium dodecylnaphthalenesulfonate in a ball mill (1 mm beads). Hemicellulose and propylene oxide were dissolved in the remaining 20% water and then the above components were added with stirring.
Example 5% oil suspension
Figure BDA0003847165890000561
Adding the above components into a kettle, stirring, and sanding with a sand mill.
Examples of measurement of biological Activity
Example 6 separate screening of active ingredients A, B and determination of the Combined Room Effect of the compositions on weeds
The combined effect of the composition on weeds was confirmed by an indoor potting test.
Quantitatively mixing gramineous weed (barnyard grass)Seeds of golden green bristlegrass, goosegrass herb) and broad-leaved weeds (zinnia elegans, velveteen) are respectively sowed in a paper cup with the diameter of 7cm and filled with nutrient soil, the sowed paper cup is covered with soil for 1cm, and the paper cup is cultivated in a greenhouse by a conventional method after being pressed and sprayed with water. Spraying stem leaves of gramineous weeds which grow to 5-7 leaf stages and broadleaf weeds which grow to 6-8 leaf stages; the pre-emergence soil spray treatment was carried out 24 hours after sowing. The spray treatment (spray pressure 1.95 kg/cm) was carried out on a crawler-type crop sprayer (Engineer Research Ltd. In England) at the experimental design dose 2 The amount of the liquid spray is 500L/hm 2 And the track speed is 1.48 km/h). The experiment was repeated 3 times. After being treated, the test material is placed in an operation hall, after the liquid medicine is naturally dried in the shade, the test material is placed in a greenhouse for management according to a conventional method, the reaction condition of the weeds to the agent is observed and recorded, and the weed control effect of the test agent is regularly observed.
The present invention evaluates the combined effect of the proposed compositions using the Colby method (s.r. Colby (1967) "calculate the synergistic and antagonistic response of a herbicide combination", weeds 15, page 22).
Theoretical value
Figure BDA0003847165890000562
In the formula:
x represents the weed control effect when the dosage of the herbicide component A is P;
y represents the weed control effect when the dosage of the herbicide component B is Q;
E 0 theoretical control when the amount of the herbicide component A is P + theoretical control when the amount of the herbicide component B is Q;
e, the actual measurement control effect of the herbicide component A and the herbicide component B after being mixed according to the proportion is obtained.
When E-E 0 >When the content is 10%, the synergistic effect is achieved; when E-E 0 <Antagonism at-10%; when E-E 0 When the value is within. + -. 10%, addition is indicated.
The bioassay results show that the compositions 1-40, 1-114-1-117, 1-120-1-122, 1-135, 1-142 and 1-154 have E-E (ethylene-propylene glycol ether) resistance to gramineous weeds, broadleaf weeds and glyphosate-resistant erigeron breviscapus and eleusine indica 0 Not less than 15 percent, has obvious synergistic effect.

Claims (8)

1. A herbicidal composition comprising an optically active phenyl isoxazoline characterized in that: the composition comprises an active component A and an active component B; wherein the active ingredient A is at least one optically active compound of the formula (I), an agriculturally acceptable salt of a compound of the formula (I) having a carboxyl group or a derivative thereof;
the active ingredient B is selected from imazethapyr, glyphosate, ammonium glyphosate, dimethylammonium glyphosate, isopropylammonium glyphosate, glufosinate ammonium, S-metolachlor, roxacin or dicamba;
the active ingredient A and the active ingredient B are 1-20;
the active ingredient A is an optically active phenylisoxazoline compound shown as a formula (I):
Figure FDA0003847165880000011
in the formula:
* Carbon represents an asymmetric carbon atom, and the configuration of the carbon atom can be R configuration (A1) or S configuration (A2);
R 1 is selected from CH 3 ；
R 2 Is selected from trifluoromethyl;
R 3 、R 4 are respectively selected from hydrogen, fluorine and chlorine;
R 5 selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl;
R 6 selected from CO 2 R 7 ；
R 7 Selected from methyl, ethyl, n-butyl and isopropyl.
2. A herbicidal composition according to claim 1, characterized in that: the active ingredient A:
* Carbon represents an asymmetric carbon atom, and the configuration of the carbon atom can be R configuration (A1) or S configuration (A2);
R 1 is selected from CH 3 ；
R 2 Is selected from trifluoromethyl;
R 3 、R 4 are respectively selected from hydrogen, fluorine and chlorine;
R 5 selected from hydrogen or methyl;
R 6 selected from CO 2 R 7 ；
R 7 Selected from methyl, ethyl, n-butyl and isopropyl.
3. A herbicidal composition according to claim 1, characterized in that: the active ingredient A is A1.
4. A herbicidal composition according to claim 1, characterized in that: the active ingredient A is A2.
5. Use of a herbicidal composition according to claim 1, characterized in that: the herbicide composition is applied to preventing and removing annual and perennial weeds, resistant or tolerant weeds in crop farmland, garden land or non-farmland.
6. A herbicidal formulation characterized by: the preparation comprises the herbicidal composition of claim 1 as an effective active ingredient, in admixture with an agriculturally acceptable carrier and at least one adjuvant; the effective component accounts for 1-99% of the weight of the preparation.
7. A herbicidal formulation according to claim 6, characterized in that: the weeding preparation is an aqueous emulsion, a dispersible oil suspending agent, a dispersible oil agent, a microemulsion, missible oil, a soluble agent, an aqueous solution, a suspending agent, a suspension emulsion, an ultra-low volume agent, powder, wettable powder, granules, water dispersible granules, dry suspending agent, microcapsule granules, effervescent tablets and water dispersible tablets.
8. Use of a herbicidal formulation according to claim 6, characterized in that: the herbicide composition is applied to preventing and removing annual and perennial weeds, resistant or tolerant weeds in crop farmland, garden land or non-farmland.
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