JPH05500063A - 除草剤性のオキサビシクロエーテル類 - Google Patents

除草剤性のオキサビシクロエーテル類

Info

Publication number: JPH05500063A
Authority: JP; Japan
Prior art keywords: compound; effective amount; plant growth; tables; alkyl
Prior art date: 1989-09-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP2512759A

Other languages

English (en)

Japanese (ja)

Inventor

パウエル，ジエイムズ・エドワード，ジユニア

リチヤードソン，ウエンデイ・スー

Original Assignee

イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-09-11

Filing date

1990-09-05

Publication date

1993-01-14

1990-09-05 Application filed by イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー filed Critical イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー

1993-01-14 Publication of JPH05500063A publication Critical patent/JPH05500063A/ja

Status Pending legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title description 10
239000004009 herbicide Substances 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims description 144
239000000203 mixture Substances 0.000 claims description 71
-1 R2 is H Chemical group 0.000 claims description 56
239000000126 substance Substances 0.000 claims description 55
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 48
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 43
238000000034 method Methods 0.000 claims description 39
230000008635 plant growth Effects 0.000 claims description 34
239000007787 solid Substances 0.000 claims description 25
230000001105 regulatory effect Effects 0.000 claims description 21
239000004094 surface-active agent Substances 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 13
239000003085 diluting agent Substances 0.000 claims description 12
239000007788 liquid Substances 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
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KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
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239000001301 oxygen Substances 0.000 claims description 4
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CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
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239000003638 chemical reducing agent Substances 0.000 description 13
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239000002689 soil Substances 0.000 description 10
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 9
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PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 1
210000003127 knee Anatomy 0.000 description 1
229940048662 kwai Drugs 0.000 description 1
CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
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150000004681 metal hydrides Chemical class 0.000 description 1
HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 1
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MYURAHUSYDVWQA-UHFFFAOYSA-N methyl n'-(4-chlorophenyl)-n,n-dimethylcarbamimidate Chemical compound COC(N(C)C)=NC1=CC=C(Cl)C=C1 MYURAHUSYDVWQA-UHFFFAOYSA-N 0.000 description 1
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235000010460 mustard Nutrition 0.000 description 1
CXUMDGLGTKUTSH-UHFFFAOYSA-N n,n-dipropyl-4-(trifluoromethyl)aniline Chemical compound CCCN(CCC)C1=CC=C(C(F)(F)F)C=C1 CXUMDGLGTKUTSH-UHFFFAOYSA-N 0.000 description 1
ZDAFHQWFOMHDMG-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-n-propanoylpropanamide Chemical compound CCC(=O)N(C(=O)CC)C1=CC=C(Cl)C(Cl)=C1 ZDAFHQWFOMHDMG-UHFFFAOYSA-N 0.000 description 1
KGMBZDZHRAFLBY-UHFFFAOYSA-N n-(butoxymethyl)-n-(2-tert-butyl-6-methylphenyl)-2-chloroacetamide Chemical compound CCCCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(C)(C)C KGMBZDZHRAFLBY-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
RJBPXZIUYLLWBF-UHFFFAOYSA-N n-phenyl-n-(2-propoxyethyl)acetamide Chemical compound CCCOCCN(C(C)=O)C1=CC=CC=C1 RJBPXZIUYLLWBF-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
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230000003000 nontoxic effect Effects 0.000 description 1
NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
SNCDZWDDKDMUES-UHFFFAOYSA-N octan-4-one Chemical compound [CH2]CCCC(=O)CCC SNCDZWDDKDMUES-UHFFFAOYSA-N 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
229940037201 oris Drugs 0.000 description 1
UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
XEEVLJKYYUVTRC-UHFFFAOYSA-N oxomalonic acid Chemical class OC(=O)C(=O)C(O)=O XEEVLJKYYUVTRC-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
210000003899 penis Anatomy 0.000 description 1
235000020030 perry Nutrition 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
ZKWPMZVVAJSYNI-UHFFFAOYSA-N prop-2-enal Chemical compound C=CC=O.C=CC=O ZKWPMZVVAJSYNI-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
MZMKPVULHIUGDS-UHFFFAOYSA-N pyridine;1,3-thiazole Chemical compound C1=CSC=N1.C1=CC=NC=C1 MZMKPVULHIUGDS-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
102220023180 rs387907415 Human genes 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
VFWRGKJLLYDFBY-UHFFFAOYSA-N silver;hydrate Chemical compound O.[Ag].[Ag] VFWRGKJLLYDFBY-UHFFFAOYSA-N 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
210000004894 snout Anatomy 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000037351 starvation Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
229910002029 synthetic silica gel Inorganic materials 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000013519 translation Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
125000002348 vinylic group Chemical group 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP2512759A 1989-09-11 1990-09-05 除草剤性のオキサビシクロエーテル類 Pending JPH05500063A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US43173489A	1989-09-11	1989-09-11
US431,734		1989-09-11

Publications (1)

Publication Number	Publication Date
JPH05500063A true JPH05500063A (ja)	1993-01-14

Family

ID=23713196

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2512759A Pending JPH05500063A (ja)	1989-09-11	1990-09-05	除草剤性のオキサビシクロエーテル類

Country Status (5)

Country	Link
EP (1)	EP0593433A1 (de)
JP (1)	JPH05500063A (de)
AU (1)	AU637406B2 (de)
CA (1)	CA2065337A1 (de)
WO (1)	WO1991003464A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR9205717A (pt) *	1991-01-30	1994-05-17	Du Pont	Éteres biciclicos herbicidas
BR9206017A (pt) *	1991-05-20	1994-08-02	Du Pont	Eteres oxatricÍclicos herbicidas
CN118005577A (zh) *	2022-11-09	2024-05-10	青岛清原化合物有限公司	一种氧杂双环烷类化合物及其制备方法、除草组合物和应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4670041A (en) *	1981-12-16	1987-06-02	E. I. Du Pont De Nemours And Company	Oxabicycloalkane herbicides
US4486219A (en) *	1983-04-21	1984-12-04	Shell Oil Company	6-Oxabicyclo[3.2.1]octane derivatives and compositions and methods for controlling plant growth
KR950001023B1 (ko) *	1986-04-14	1995-02-07	셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이	할로겐화 헤테로시클릭 에테르 제초제 제조방법
US4798621A (en) *	1986-10-10	1989-01-17	E. I. Du Pont De Nemours And Company	Selective method-of-use of oxabicycloalkanes
BR8807695A (pt) *	1987-09-15	1990-08-07	Du Pont	Oxabicicloalcanos seletivos
KR900701793A (ko) *	1988-05-23	1990-12-04	제임스 제이. 플린	제초제 옥사비사이클로알칸 에테르
PT93107A (pt) *	1989-02-10	1990-08-31	Du Pont	Processo para a preparacao de novos derivados etereos de oxabiciclononano com accao herbicida

1990
- 1990-09-05 EP EP90913636A patent/EP0593433A1/de not_active Withdrawn
- 1990-09-05 AU AU63474/90A patent/AU637406B2/en not_active Ceased
- 1990-09-05 CA CA 2065337 patent/CA2065337A1/en not_active Abandoned
- 1990-09-05 WO PCT/US1990/004953 patent/WO1991003464A1/en not_active Ceased
- 1990-09-05 JP JP2512759A patent/JPH05500063A/ja active Pending

Also Published As

Publication number	Publication date
EP0593433A1 (de)	1994-04-27
CA2065337A1 (en)	1991-03-12
AU637406B2 (en)	1993-05-27
AU6347490A (en)	1991-04-08
WO1991003464A1 (en)	1991-03-21

Publication	Publication Date	Title
US4881967A (en)	1989-11-21	Heterocyclic 2,3-dihydrobenzofuran herbicides
US5510318A (en)	1996-04-23	Herbicidal oxazine ethers
US5356862A (en)	1994-10-18	Herbicidal sulfonylureas
WO1990001030A1 (en)	1990-02-08	Substituted phenyltriazolopyrimidine herbicides
US4946494A (en)	1990-08-07	Herbicidal pyridine sulfonylureas
WO1993003020A1 (en)	1993-02-18	Herbicidal quinoxalinyloxy ethers
US5125954A (en)	1992-06-30	Herbicidal oxabicycloalkane ethers
JPH05500063A (ja)	1993-01-14	除草剤性のオキサビシクロエーテル類
US4921527A (en)	1990-05-01	Herbicidal sulfonamides
US4828603A (en)	1989-05-09	Herbicidal oxatricyclo-nonane ethers
US5053071A (en)	1991-10-01	Chromane herbicides
US4758262A (en)	1988-07-19	Herbicidal propylene oxide derivatives
WO1992013861A1 (en)	1992-08-20	Herbicidal bicyclic ethers
EP0301919A2 (de)	1989-02-01	Herbizide Sulfonamide
US4948418A (en)	1990-08-14	2,3-dihydrobenzo[b]thiophenes
WO1990009383A1 (en)	1990-08-23	Herbicidal oxabicyclononane ethers
US5175314A (en)	1992-12-29	Herbicidal oxatricyclic ethers
US5234900A (en)	1993-08-10	Herbicidal oxabicyclo ethers
WO1990010634A1 (en)	1990-09-20	Selective oxabicycloalkanes
US5407901A (en)	1995-04-18	Herbicidal oxatricyclic ethers
US4881968A (en)	1989-11-21	Herbicidal sulfonamides
US4995901A (en)	1991-02-26	Herbicidal sulfonamides
WO1990012012A1 (en)	1990-10-18	Substituted phenyltriazolopyrimidine herbicides
WO1992003440A1 (en)	1992-03-05	Herbicidal ethers
JPH05194495A (ja)	1993-08-03	除草性ピラゾールスルホンアミド類