DK144526B - Herbicide 3-alkylisoxazolderivater og salte derzf - Google Patents
Herbicide 3-alkylisoxazolderivater og salte derzf Download PDFInfo
- Publication number
- DK144526B DK144526B DK443575AA DK443575A DK144526B DK 144526 B DK144526 B DK 144526B DK 443575A A DK443575A A DK 443575AA DK 443575 A DK443575 A DK 443575A DK 144526 B DK144526 B DK 144526B
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- DK
- Denmark
- Prior art keywords
- weight
- parts
- butyl
- isoxazolyl
- urea
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims description 15
- 239000004009 herbicide Substances 0.000 title claims description 11
- 150000002545 isoxazoles Chemical class 0.000 claims description 9
- -1 1-Methoxy-1-methoxy-3- (3-i-propyl-5-isoxazolyl) urea Chemical compound 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000004927 clay Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- KMEKZESIISVXOI-UHFFFAOYSA-N 1-butyl-3-(3-tert-butyl-1,2-oxazol-5-yl)-1-methylurea Chemical compound CCCCN(C)C(=O)NC1=CC(C(C)(C)C)=NO1 KMEKZESIISVXOI-UHFFFAOYSA-N 0.000 claims description 2
- IULHFTFLQZBCNR-UHFFFAOYSA-N 3-(3-tert-butyl-1,2-oxazol-5-yl)-1-methoxy-1-methylurea Chemical compound CON(C)C(=O)NC1=CC(C(C)(C)C)=NO1 IULHFTFLQZBCNR-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- YQCBAZGXYYXJJH-UHFFFAOYSA-N s-methyl n-(3-tert-butyl-1,2-oxazol-5-yl)carbamothioate Chemical compound CSC(=O)NC1=CC(C(C)(C)C)=NO1 YQCBAZGXYYXJJH-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
(19) DANMARK fHj
W) (12) FREMLÆGGELSESSKRIFT ου 144526 B
DIREKTORATET FOR PATENT- OG VAREMÆRKEVÆSENET
(21) Ansøgning nr. ^435/75 (51) |nt.CI.3 C 07 D 261/14 (22) Indleveringsdag 1 · °kt. 1975 A 01 N 47/08 (24) Løbedag 1 . okt. 1975 (41) Aim. tilgængelig 5· apr. 1976 (44) Fremlagt 22. mar. 1982 (86) International ansøgning nr. “ (86) International indleveringsdag -(85) Videreførelsesdag -(62) Stamansøgning nr. -
(30) Prioritet 4. okt. 1974, 114839/74, JP
(71) Ansøger SHIONOGI & CO. LTD., Osaka, JP.
(72) Opfinder Hisajiro jftikinaga, JP: Shinzaburo Sumimoto, JP: Ichiro JCshizuka, JP: Jitsuo Sugita, JP.
(74) Fuldmægtig Th. Ostenfeld Patentbureau A/S.
(54) Herbicide 3-alkylisoxazolderiva= fcer og salte deraf.
Den foreliggende opfindelse angår hidtil ukendte 3-alkylisoxa-zolderivater med den almene formel:
XH-T“R
DO R1 II
-O 2/N-(I) N R r
-O
d- d- r— ^ hvori R betegner i α-stillingen forgrenet C3_6 alkyl, R1 betegner
D
2 144526 R3 2 3
hydrogen eller C, 0 alkyl, R betegner gruppen -C-N . , hvori R
1-3 H Nr4
4 Y
og R hver for sig betegner hydrogen, C-^_g alkyl eller C^_galkoxy, 5 5 og Y betegner oxygen eller svovl,eller gruppen -CO-Y-R , hvori R betegner C^_^alkyl, og Y er som defineret ovenfor, og X betegner hydrogen, halogen eller C^g alkyl, og herbicidt aktive salte deraf.
Fra beskrivelsen til USA patenter nr.3.547.940 og 3.743.498 er det kendt, at visse 3-methyl-5-isoxazolyl-urinstof- og 3-ethyl-5-isoxazolylurinstofderivater besidder herbicid aktivitet.
Ved undersøgelser af den herbicide aktivitet af forskellige iso-xazolderivater har det nu vist sig, at isoxazol-derivaterne (I) med i α-stillingen forgrenet C3_galkyl i 3-stillingen udviser langt stærkere herbicid aktivitet end de nævnte kendte urinstofderivater, samtidig med at toksiciteten over for mennesker, husdyr, fjerkræ, fisk og skaldyr er meget lille, ligesom de let nedbrydes i jorden.
3-alkylisoxazol-derivaterne (I) ifølge den foreliggende opfindelse omfatter to typer forbindelser (urinstof-typen og carbamat-typen). Urinstof-typen har formlen: r3 X”T1-iPR (Ia)
Nj-c-n_l R^ £ ^1 S)'"* 13 4 hvori R, R , R , R , X og Y hver for sig er som defineret ovenfor, og carbamat-typen har formlen: X—π-f]—R (Ib) R5- Y - CON-L n •i-o-' hvori R, R·*", R^, X og Y hver for sig er som defineret ovenfor. Disse isoxazol-derivater (I), (la) og (Ib) kan fremstilles efter følgende reaktionsskemaer:
Metode 1 3 144526
pi ΓΤ-E < XJ~TS
-li m ^0> halogenerinq ^ 0 (I) (X=hydrogen) (I) (X= halogen)
Denne metode består i halogenering i 4-stillingen af isoxazolringen f.eks. chlorering, bromering, og iodering. Disse reaktioner udføres på konventionel måde under anvendelse af almindelige halogeneringsmidler, katalysatorer, opløsningsmidler og temperaturbetingelser.
Metode 2
< *ίγτ* < *ίγίrR
2/ H-^ 0 ^ r2/H-^ 0-S
N-alkylering ^ [Her findes mindst [Mindst en alkylgruppe et hydrogen på nitro- er indført på nitrogenet] genet i sidekæden]
Denne metode består i alkylering af det aktive nitrogen i sidekæden. Almindelige N-alkyleringsmidler kan generelt benyttes. F.eks. kan til methylering benyttes methylhalogenid (f .ex.methylbromid, methyliodid), dimethylsulfat, diazomethan,organiske sulfonsyreestere (f.eks. methyl-methansulfonat, methyltoluensulfonat), en blanding af formaldehyd og myresyre eller en blanding af formaldehyd og et reduktionsmiddel. N-alkyleringen kan udføres på konventionel måde.
Metode 3
X-i-j|—R 3 X—i-|i— R
O™ rW (III) . ^C0NH-l0/ (II) (la) (R^hydrogen Y=oxygen)
Denne metode kan udføres ved at omsætte 5-isoxazolylisocyanatet (II) med aminen (III) i et inert opløsningsmiddel (f.eks. benzen, toluen, 4 144526 dioxan, diglym, dimethylformamid) ved stuetemperatur eller under køling eller under opvarmning, om nødvendigt i tilstedeværelse af en basisk katalysator (f.eks. pyridin, triethylamin).
Metode 4
X-|-rø-K *Tj-[pR
Η1-^-R3_NCi (v) R3-NH-C-N-^0^.
(IV) 7 Y R1 4 (la) (R =hydrogen)
Denne metode kan udføres ved at omsætte aminen (IV) med isocyana-tet eller isothiocyanatet (V). Reaktionen udføres som ved metode 3.
Metode 5 ΧΊ—ΓΕ r3 X1—[Γ® R3HH-COtt- or4-r (VI) , ^-CO-N—
R± ? R
(la)(R4=hydrogen (la) (R4=alkylthio Y =oxygen) Y =oxygen) hvori A betegner en reaktiv gruppe (f.eks. halogen eller en esterrest). Denne metode udføres ved at behandle urinstoffet (la) indeholdende et aktivt nitrogenatom med reagenset (VI), som f.eks. kan være et alkyl-sulfenylhalid, i et egnet opløsningsmiddel (f.eks. pyridin, benzen) ved stuetemperatur eller under køling.
Metode 6
x_l rR χί rR
OCN-k 0^N R5-Y-H (VII) ^ R5-Y-CONH<-lX0^N
(II) (Ib)(R1=hydrogen)
Metoden udføres ved at omsætte 5-isoxazolylisocyanatet (II) med alkoholen eller mercaptanen (VII). Reaktionen udføres som ved metode 3.
5 U4526
Metode 7
χ—η—|pR ΧΊ-Π-R
Ε1-ΚΗ_1^ο^ r5-OCO-A (VIII) H-0-CO^-^ (IV) (Ib) (Y=oxygen)
Denne metode udføres ved at omsætte 5-isoxazolylaminen (IV) med et reaktivt derivat (f .eks. halogenid, ester) af kulsyre (VIII) under tilstedeværelse af en base (f.eks. pyridin, triethylamin) eventuelt i et inert opløsningsmiddel (f.eks. dimethylformamid, chloroform, tetra-hydrofuran, benzen) ved stuetemperatur eller under opvarmning.
Fremstillingen af de omhandlede isoxazolderivater (I) belyses nærmere i de følgende eksempler.
Eksempel 1
Til en opløsning af 3-t-butyl-5-isoxazolylisocyanat (2,84 g) i toluen (51 ml) sættes methylamin (1,58 g) ved stuetemperatur. Blandingen omrøres ved stuetemperatur i 2 timer og derefter ved 50°C i 4 timer. Reaktionsblandingen inddampes, og remanensen omkrystalliseres fra ethyl-acetat, hvorved fås 1-methy1-3-(3-t-butyl-5-isoxazolyl)urinstof (2,80 g) som krystaller, der smeltede ved 195,0 - 196,0°C (dekomponering). Udbyttet er 83,6%.
Eksempler 2-8
Under anvendelse af følgende udgangsmaterialer (II) udføres reaktionerne som i eksempel 1, hvorved de tilsvarende produkter (la) fås.
—rE < xirirR
OCN-^ ___i . nCONH -k, Ji
O ' O
(II) (la) 5 144526
Tabel 1 H__3_4_Ϊ2--
Eksempel nr. R R R Smp.
2 i-Pr H Me 163,0—164,0 3 i-Pr Me Al 51,5-52,5 4 i—Pr Me Met 80,0—81,0 5 t-Bu Η H 176,0-177,0(d) 6 t-Bu Me Me 125,5-126,0 7 t-Bu Me Bu 86,0-87,0 8 t-Bu Me Met 105,5-106,0
Bemærkning: Forkortelserne i tabellen har følgende betydninger: H (hydrogen) , Me (methyl), Pr (propyl), Bu (butyl),
Met (methoxy), Al (allyl), i- (iso) , t -(tertiær-), smp. (smeltepunkt °C).
Eksempel 9
En blanding af 3-t-butyl-5-methylarninoisoxazol (2,16 g) og methyl-isocyanat (1,04 g) opvarmes til 80°C i et tilsmeltet rør i 13 timer. Derefter tilsættes methylisocyanat (0,40 g), og den fremkomne blanding opvarmes til 80°C i 9 timer. Reaktionsblandingen kromatograferes på en søjle af silicagel, hvorved der fås 1,3-dimethyl-3-(3-t-butyl-5-isoxazolyl)-urinstof (2,56 g). Udbyttet er 86,3%. IR: 1700, 1598 cm ^ (CC14).
Eksempel 10
Til en opløsning af 3-t-butyl-5-isoxazolylisocyanat (11,63 g) i toluen (154 ml) sættes methanol (20 ml) og triethylamin (3 dråber), og den fremkomne blanding omrøres ved 80°C i 3 timer. Reaktionsblandingen inddampes, for at fjerne lavtkogende stoffer, og remanensen omkrystalliseres fra n-hexan, hvorved fås methyl-3-t-butyl-5-isoxazolylcarbamat (12,17 g) som krystaller, der smelter ved 86,5 - 87°C.
Eksempel 11 7 144526
Under anvendelse af 3-t-butyl-5-isoxazolylisocyanat og methyl-mercaptan udføres reaktionen som i eksempel 1Q, hvorved der fås S-methyl-3-t-butyl-5-isoxazolylthiocarbamat som krystaller, der smelter ved 104,0 til 105,5°C.
Eksempel 12
Til en opløsning af natrium (0,42 g) i methanol (12 ml) sættes en opløsning af methyl 3-t-butyl-5-isoxazolylcarbamat (3,47 g) i methanol (5,5 ml), og den fremkomne blanding omrøres ved stuetemperatur i 10 minutter. Reaktionsblandingen inddampes under reduceret tryk for at fjerne methanolen. Remanensen tilsættes benzen, som igen fjernes ved inddampning. Remanensen tilsættes igen benzen (27 ml), og dime thylsulf at (2,32 g) tilsættes dråbevis. Den fremkomne blanding omrøres ved stuetemperatur i 1 time og koges derefter under tilbagesvaling i 1 time. Efter afkøling filtreres reaktionsblandingen for at fjerne bundfaldet. Filtratet vaskes med vandig natriumbicarbonat og vand i denne rækkefølge, tørres med vandfri natriumsulfat og inddampes. Remanensen omkrystalliseres fra cyclohexanon, hvorved fås methyl-N-methyl-3-t-butyl-5-isoxazolylcarbamat (3,41 g) som krystaller, der smelter ved 70,5 til 71,5°C. Udbyttet er 91,8%.
Eksempel 13
Ved omsætning af 1,1-dimethy1-3-(3-t-butyl-5-isoxazolyl)urinstof med methyliodid i dimethylformamid i nærværelse af natriumhy-drid fås l,l,3-trimethyl-3-(3-t-butyl-5-isoxazolyl)urinstof som krystaller, der smelter ved 72,0 til 73,0°C.
Eksempel 1^.
Til en blanding af 1,1-dimethy1-(3-t-butyl-5-isoxazolyl)urinstof (0,70 g), vandfri natriumacetat (0,30 g) og iseddike (3,3 ml), sættes dråbevis brom (0,53 g) i løbet af 10 minutter under isafkøling og omrøring, og den fremkomne blanding omrøres i 15 minutter. Reaktionsblandingen hældes i isvand (30 ml) og udrystes med methylenchlorid. Den organiske fase vaskes med mættet vandig natriumbicarbonatopløsning og vand i nævnte rækkefølge og inddampes. Remanensen omkrystalliseres fra benzen, hvorved fås 1,1-dimethy1-3-(3-t-butyl-4-brom-5-isoxazolyl)-urinstof (0,96 g) som krystaller, der smelter ved 175,5 til 176,5°C (dekomponering).
8 144526
Eksempel 1$
Til en opløsning af methyl-3-t-butyl-5-isoxazolylcarbamat (2,56 g) i methylenchlorid (13 ml) sættes dråbevis sulfurylchlorid (1,81 g), og den fremkomne blanding koges under tilbagesvaling i 2 timer. Reaktionsblandingen inddampes, hvorved fås methyl-3-t-butyl-4-chlor-5-isoxazolyl-carbamat (3,08 g) i form af en olie. IR: 1748, 1642 cm ^ (CCl^).
Eksempel 16
Under anvendelse af 1-methy1-3-(3-t-butyl-5-isoxazolyl)urinstof udføres reaktionen som i eksempel 16, hvorved l-methyl-3-(3-t-butyl-4-chlor-5-isoxazolyl)urinstof fås som krystaller, der smelter ved 169,0 til 170,5°C (dekomponering).
Eksempel 17
En blanding af 3-t-butyl-5-aminoisoxazol (2,07 g), methylisothio-cyanat (1,40 g) og trlethylamin (3 dråber) opvarmes til 75°C i 72 timer. Reaktionsblandingen kromatograferes på en søjle af silicagel, hvorved l-methyl-3-(3-t-butyl-5-isoxazolyl)thiourinstof (1,66 g) fås somen olie. IR: 1622 cm ^ (CCl^).
Isoxazolderivaterne (I) ifølge opfindelsen udviser en yderst god herbicid virkning overfor forskellige græsser ved en lav dosis, og de kan anvendes som non-selektive eller selektive herbicider ved ændring af den anvendte dosis af den aktive forbindelse. Herbiciderne ifølge opfindelsen kan anvendes generelt ved forskellige afgrøder, herunder hvede, byg, majs, gulerod, jordnød, ærter eller ris. De kan anvendes på sukkerrør, kartofler, søde kartofler, mynte, ægplante eller spansk paprika efter plantning. Forbindelserne ifølge opfindelsen bevirker ingen eller næsten ingen kemiske beskadigelser på disse afgrøder. Eventuelle beskadigelser er under alle omstændigheder så lette, at planten let kommer over dem. Forbindelserne er uskadelige overfor mennesker, husdyr 144526 9 og fjerkræ og har en meget lav giftvirkning overfor fisk og skaldyr. Forbindelserne ifølge den foreliggende opfindelse er derfor meget sikre og udviser en passende residualgrad i jorden.
Herbicid-præparater indeholdende forbindelser ifølge opfindelsen kan fremstilles ved at blande det aktive isoxazol-derivat (I) med et egnet inert fast eller flydende bæremiddel, og eventuelt andre hjælpestoffer (f.eks. emulgeringsmidler, stabilisatorer, dispergeringsmidler, suspensionsmidler, spredemidler, indtrængningsmidler, befugtningsmidler) og omdanne den fremkomne blanding til den ønskede slags præparat (f.eks. emulsioner, befugteligt pulver, granula, puddere, piller). Eksempler på bæremidler er et fast bæremiddel (f.eks. ler, talkum, diatoméjord, bentonit) og et flydende bæremiddel (f.eks. vand, alkoholer, acetone, benzen, toluen, xylen, naphtha, cyclohexan).
Isoxazolderivateme ifølge den. foreliggende opfindelse kan også anvendes sammen med landbrugskemikalier (f.eks. insekticider, fungicider, andre herbicider), gødningsstoffer (f.eks. ammoniumsulfat, urinstof) eller jordbehandlingsmidler.
Den herbicide virkning af de omhandlede isoxazolderivater illustreres i følgende eksperimentelle eksempel.
Eksperimentelt eksempel a) AFPRØVEDE FORBINDELSER:
Forbindelse nr. Navn 1 l-methyl-l-butyl-3-(3-t-butyl-5-isoxazolyl)urinstof 2 l-methyl-3-(3-t-butyi-5-isoxazolyl)urinstof 3 1,l-dimethyl-3-(3-t-butyl-5-isoxazolyl)urinstof 4 l,l,3-trimethyl-3-(3-t-butyl-5-isoxazolyl)urinstof 5 1,3-dimethyl-3-(3-t-butyl-5-isoxazolyl)urinstof 6 l-methyl-l-methoxy-3-(3-t-butyl-5-isoxazolyl)urinstof 7 l-methyl-l-methoxy-3-(3-i-propyl-5-isoxazolyl)urinstof 8 methyl-N-(3-t-butyl-4-chlor-5-isoxazolyl)carbamat 9 l-methyl-3-(3-t-butyl-4-chlor-5-isoxazolyl)urinstof 10 1,l-dimethyl-3-(3-t-butyl-4-brom-5-isoxazolyl)urinstof 11 PCP-Na (natriumpentachlorphenoxid) (kommercielt tilgængeligt herbicid) 12 l-phenyl-3-(3-methyl-4-brom-5-isoxazolyl)urinstof (forbindelse beskrevet i U.S.A. patentskrift nr. 3.547.940) 10 144526 b) AFPRØVNINGSMETODE: (1) Afprøvning før tilsynekomst: I et polyethylenbæger (diameter: 9 cm), hvor der var anbragt sandet jord, blev sået 25 frø af hver slags afprøvet plante. Efter såning dækkedes frøene med sandet jord i en tykkelse på ca. 5 mm og kort efter spredtes en vandig opslæmning af den afprøvede forbindelse i en koncentration på 100 dpm ud over overfladen af den sandede jord. Dosen af den anvendte forbindelse var 10 g/ar og 30 g/ar, og den vandige opslæmning (fortynding i vand : 10 liter/ar) spredtes med en spreder. Forsøget udførtes ved 25°C i et væksthus i naturligt sollys. Spiringsgraden måltes 3 uger efter anvendelse.
(2) Afprøvning efter tilsynekomst:
Som ved afprøvningen før tilsynekomst anvendtes den afprøvede forbindelse på unge planter 10 dage efter såning. Spredning og måling udførtes som beskrevet ovenfor.
c) VURDERING:
Resultaterne indsamledes ved at observere planten med det blotte øje efter anvendelse af herbicidet og beregne brøkdelen af levende planter tre uger senere. Ved vurderingen inddeltes der i 6 grupper efter overlevelsesprocenten som følger:
Overlevelsesprocent af den afprøvede plante Betegnelse
Ikke over 10% 5 11-25% 4 26-50% 3 51-75% 2 76-90% 1 91-100% 0
Tabel 2 146526 u d) RESULTATER:
Forbin- Anvendel- _Herbicid virkning__ delse sesdosis Afprøvning før Afprøvning efter nr. (g/ar) tilsynekomst tilsynekomst
_A B C D E F_A B C D E F
10 033555 033555 _30_0 5 3 5 5 5_0 5 5 5 5 5 10 002435 023555 __30_0 2 4 5 5 5_0 3 5 5 5 5 10 014555 134555 ~_30_1 3 5 5 5 5_1 5 5 5 5 5 . 10 012553 000555 __30_0 1 3 5 5 4_0 1 2 5 5 5 _ 10 025555 033555 __30_0 3 4 5 5 5_0 5 5 5 5 5 - 10 035555 022555 __30_0 5 5 5 5 5_0 5 5 5 5 5 , 10 003255 001545 __30_0 3 5 5 5 5_0 2 3 5 5 5 10 000444 000225 __30_0 1 2 5 5 5_0 115 5 5 10 024555 002514 __30_0 2 5 5 5 5_0 1 2 5 3 5 in 10 000404 011545 __30_0 1 1 5 5 5_0 115 5 5 10 000023 000025 _30_0 0 0 0 2 3_0 0 0 0 4 5 1 000011 000001 __30_0 0 0 0 0 2_0 0 0 0 0 0
Bemærk: De anvendte forkortelser har følgende betydninger: A (Triticum aestivum), B (Echinochloa crusgalli), C (Digitaria adscendens), D (Brassica campestris), E (Polygonum logisetum), F (Amaranthus retroflexus).
Følgelig udviser forbindelserne ifølge opfindelsen (forbindelser nr. 1-10) næppe alle herbicid-virkning overfor Triticum aestivum men udviser generelt en yderst god og selektiv herbicid-virkning overfor Echinochloa crusgalli, Digitaria adscendens, Brassica campestris, Polygonum longisetum og Amaranthus retroflexus og er langt mere virkningsfuld end PCP-Na (forbindelse nr. 11), et kommercielt tilgængeligt herbicid og 1-phenyl-3-(3-methyl-4-brom-5-isoxazolyl)urinstof (forbindelse nr. 12) beskrevet I U.S.A. patentskrift nr. 3.547.940.
Claims (1)
12 144526 Fremstilling af herbicid-præparater indeholdende isoxazol-derivater ifølge opfindelsen illustreres i de følgende eksempler. Eksempel A. l-methyl-l-butyl-3-(3-t-butyl-5-isoxazolyl)urinstof (10 vægtdele), "Sorpol" (registreret varemærke; fremstillet af Toho Chemical Industry, Co., Ltd.) (10 vægtdele), cyclohexanon (20 vægtdele) og naphtha (60 vægtdele) blandes og opløses, hvorved der fås en emulsion. Eksempel B l,l,3-trimethyl-3-(3-t-butyl-5-isoxazolyl)urinstof (50 vægtdele), calciumligninsulfonat (3 vægtdele), "Sorpol" (registreret varemærke; fremstillet af Toho Chemical Industry, Co., Ltd.) (3 vægtdele) og diatoméjord (44 vægtdele) blandes og pulveriseres, hvorved der fås et befugteligt pulver. Eksempel C l-methyl-l-methoxy-3-(3-t-butyl-5-isoxazolyl)urinstof (5 vægtdele) og ler (95 vægtdele) blandes og pulveriseres, hvorved der fås et pulver. Eksempel D l-methoxy-l-methoxy-3-(3-i-propyl-5-isoxazolyl)urinstof (5 vægtdele) , calciumligninsulfonat (5 vægtdele), bentonit (30 vægtdele) og ler (60 vægtdele) blandes og pulveriseres, blandes med vand, æltes, granuleres og tørres, hvorved der fås et granulat. Herbicide 3-alkylisoxazolderivater, KENDETEGNET ved, at de har den almene formel: X—-π—R R\ jj 9/n- R5^
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11483974 | 1974-10-04 | ||
| JP49114839A JPS5810361B2 (ja) | 1974-10-04 | 1974-10-04 | ３−アルチルイソオキサゾ−ル系除草剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK443575A DK443575A (da) | 1976-04-05 |
| DK144526B true DK144526B (da) | 1982-03-22 |
| DK144526C DK144526C (da) | 1982-10-04 |
Family
ID=14647980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK443575A DK144526C (da) | 1974-10-04 | 1975-10-01 | Herbicide 3-alkylisoxazolderivater og salte deraf |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4028376A (da) |
| JP (1) | JPS5810361B2 (da) |
| AR (1) | AR220094A1 (da) |
| BR (1) | BR7506453A (da) |
| CA (1) | CA1049516A (da) |
| CH (1) | CH595762A5 (da) |
| DE (1) | DE2544367A1 (da) |
| DK (1) | DK144526C (da) |
| FR (1) | FR2286820A1 (da) |
| GB (1) | GB1463439A (da) |
| IT (1) | IT1047275B (da) |
| MX (1) | MX3245E (da) |
| NL (1) | NL7511694A (da) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5031039A (da) * | 1973-07-27 | 1975-03-27 | ||
| US4111680A (en) * | 1973-07-27 | 1978-09-05 | Shionogi & Co., Ltd. | Herbicidal compositions containing 3-isoxazolylurea derivatives |
| JPS6033109B2 (ja) * | 1977-04-28 | 1985-08-01 | 塩野義製薬株式会社 | 尿素誘導体の合成法 |
| FR2392981A1 (fr) * | 1977-05-31 | 1978-12-29 | Philagro Sa | Thiolcarbamates d'(isoxazolyl)-alcoyles et compositions herbicides les contenant |
| EP0002881A1 (en) * | 1977-11-02 | 1979-07-11 | FISONS plc | 5-Isoxazolylurea derivatives, their preparation, their use and compositions containing them |
| JPS607988B2 (ja) * | 1978-10-12 | 1985-02-28 | 塩野義製薬株式会社 | ３―アミノ―５―第三ブチルイソオキサゾールの改良合成法 |
| US4336264A (en) * | 1980-06-19 | 1982-06-22 | Eli Lilly And Company | 1-Benzoyl-3-(isoxazolyl or benzisoxazolyl)-ureas and insecticidal use thereof |
| US4394510A (en) * | 1981-02-02 | 1983-07-19 | Eli Lilly And Company | Process for preparing an isoxazolylurea |
| IT1163183B (it) * | 1983-03-29 | 1987-04-08 | Anic Spa | Composti eterociclici ad attivita' erbicida |
| US4689071A (en) * | 1983-05-05 | 1987-08-25 | Ppg Industries, Inc. | Herbicidally active 3-isoxazolyl-2-imidazolidinone derivatives |
| US4544753A (en) * | 1984-05-31 | 1985-10-01 | Hoechst-Roussel Pharmaceuticals Incorporated | Isoxazole intermediates |
| DE3818556A1 (de) * | 1988-06-01 | 1989-12-07 | Pfeiffer Vakuumtechnik | Magnetlager fuer eine schnell rotierende vakuumpumpe |
| EP0427963B1 (de) * | 1989-11-10 | 1994-03-30 | Agrolinz Agrarchemikalien Gesellschaft M.B.H. | Verfahren zur Herstellung reiner, unsymmetrisch disubstituierter Harnstoffe |
| DE3940261A1 (de) * | 1989-12-06 | 1991-06-13 | Agrolinz Agrarchemikalien Muen | Verfahren zur herstellung reiner, unsymmetrisch disubstituierter harnstoffe |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3743498A (en) * | 1967-10-31 | 1973-07-03 | Du Pont | Method of selectively controlling undesirable vegetation |
| US3547940A (en) * | 1967-10-31 | 1970-12-15 | Du Pont | Substituted ureido isoxazoles |
-
1974
- 1974-10-04 JP JP49114839A patent/JPS5810361B2/ja not_active Expired
-
1975
- 1975-09-23 US US05/615,883 patent/US4028376A/en not_active Expired - Lifetime
- 1975-09-26 CA CA236,477A patent/CA1049516A/en not_active Expired
- 1975-10-01 GB GB4020575A patent/GB1463439A/en not_active Expired
- 1975-10-01 DK DK443575A patent/DK144526C/da not_active IP Right Cessation
- 1975-10-03 CH CH1289575A patent/CH595762A5/xx not_active IP Right Cessation
- 1975-10-03 NL NL7511694A patent/NL7511694A/xx not_active Application Discontinuation
- 1975-10-03 DE DE19752544367 patent/DE2544367A1/de not_active Ceased
- 1975-10-03 IT IT69469/75A patent/IT1047275B/it active
- 1975-10-03 FR FR7530435A patent/FR2286820A1/fr active Granted
- 1975-10-03 MX MX000867U patent/MX3245E/es unknown
- 1975-10-03 AR AR260670A patent/AR220094A1/es active
- 1975-10-03 BR BR7506453*A patent/BR7506453A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK443575A (da) | 1976-04-05 |
| DK144526C (da) | 1982-10-04 |
| IT1047275B (it) | 1980-09-10 |
| JPS5141431A (da) | 1976-04-07 |
| GB1463439A (da) | 1977-02-02 |
| FR2286820A1 (fr) | 1976-04-30 |
| DE2544367A1 (de) | 1976-04-22 |
| CA1049516A (en) | 1979-02-27 |
| BR7506453A (pt) | 1976-08-10 |
| NL7511694A (nl) | 1976-04-06 |
| FR2286820B1 (da) | 1979-04-20 |
| AU8551475A (en) | 1977-04-21 |
| MX3245E (es) | 1980-08-06 |
| US4028376A (en) | 1977-06-07 |
| JPS5810361B2 (ja) | 1983-02-25 |
| CH595762A5 (da) | 1978-02-28 |
| AR220094A1 (es) | 1980-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |